fix: enforce scoped GCP Leo runtime credentials

2026-07-15 04:40:26 +02:00 · 2026-07-15 04:40:26 +02:00 · b7bdcea46a
commit b7bdcea46a
parent 68625b8afa
14 changed files with 5031 additions and 224 deletions
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@ -52,6 +52,8 @@ jobs:
            ops/restore_gcp_generated_postgres_snapshot.py \
            ops/sqlite_to_postgres_dump.py \
            ops/verify_gcp_cloudsql_restore_readback.py \
+            ops/verify_gcp_leoclean_runtime_permissions.py \
+            ops/verify_gcp_leoclean_service_environment.py \
            ops/verify_postgres_parity_manifest.py \
            telegram/approvals.py \
            hermes-agent/leoclean-bin/kb_tool.py \
@ -80,6 +82,8 @@ jobs:
            tests/test_capture_vps_canonical_postgres_snapshot.py \
            tests/test_gcp_infra_execute_canary.py \
            tests/test_gcp_infra_readiness_checker.py \
+            tests/test_gcp_leoclean_runtime_permissions.py \
+            tests/test_gcp_leoclean_service_environment.py \
            tests/test_gcp_runtime_baseline_apply.py \
            tests/test_gcp_service_communications.py \
            tests/test_gcp_cloudsql_restore_drill.py \
@ -102,12 +106,15 @@ jobs:
            tests/test_restore_gcp_generated_postgres_snapshot.py \
            tests/test_sqlite_to_postgres_dump.py \
            tests/test_sqlite_postgres_restore_canary_capsule.py \
+            tests/test_teleo_agent_systemd.py \
            tests/test_eval_parse.py \
            tests/test_contributor.py \
            tests/test_search.py
      - name: Shell syntax
        run: |
          bash -n \
+            deploy/sync-gcp-leoclean-runtime.sh \
+            hermes-agent/leoclean-bin/teleo-kb \
            ops/backup_vps_sqlite_kb.sh \
            ops/run_gcp_cloudsql_restore_drill.sh \
            ops/run_sqlite_postgres_restore_canary.sh
--- a/deploy/sync-gcp-leoclean-runtime.sh
+++ b/deploy/sync-gcp-leoclean-runtime.sh
@ -10,23 +10,28 @@ ZONE="${ZONE:-europe-west6-a}"
 INSTANCE="${INSTANCE:-teleo-prod-1}"
 SERVICE="${SERVICE:-leoclean-gcp-prod-parallel.service}"
 MERGED_REF="${MERGED_REF:-origin/main}"
-REMOTE_PROFILE_BIN="${REMOTE_PROFILE_BIN:-/home/teleo/.hermes/profiles/leoclean/bin}"
+REMOTE_RUNTIME_BIN="${REMOTE_RUNTIME_BIN:-/usr/local/libexec/livingip/leoclean-kb}"
+SERVICE_PROFILE_BIN="${SERVICE_PROFILE_BIN:-/home/teleo/.hermes/profiles/leoclean/bin}"
+SERVICE_PROFILE_ROOT="${SERVICE_PROFILE_ROOT:-/home/teleo/.hermes/profiles/leoclean}"
+SERVICE_HERMES_ROOT="${SERVICE_HERMES_ROOT:-/home/teleo/.hermes}"
 REMOTE_DROPIN_DIR="${REMOTE_DROPIN_DIR:-/etc/systemd/system/$SERVICE.d}"
-REMOTE_CLOUDSDK_CONFIG="${REMOTE_CLOUDSDK_CONFIG:-/run/leoclean-gcp-prod-parallel}"
 EXPECTED_VM_SERVICE_ACCOUNT="${EXPECTED_VM_SERVICE_ACCOUNT:-sa-teleo-prod-vm@teleo-501523.iam.gserviceaccount.com}"

 WRAPPER_REL="hermes-agent/leoclean-bin/teleo-kb"
 TOOL_REL="hermes-agent/leoclean-bin/cloudsql_memory_tool.py"
+PERMISSION_VERIFIER_REL="ops/verify_gcp_leoclean_runtime_permissions.py"
+SERVICE_ENV_VERIFIER_REL="ops/verify_gcp_leoclean_service_environment.py"
 DROPIN_REL="systemd/leoclean-gcp-prod-parallel-cloudsql.conf"
 DROPIN_NAME="10-cloudsql-memory.conf"

 DRY_RUN=false
 RESTART=false
 VERIFY_ONLY=false
+PREFLIGHT_ONLY=false

 usage() {
  cat <<'USAGE'
-Usage: deploy/sync-gcp-leoclean-runtime.sh [--dry-run] [--restart] [--verify-only]
+Usage: deploy/sync-gcp-leoclean-runtime.sh [--dry-run] [--preflight-only] [--restart] [--verify-only]

 The database role and scoped Secret Manager secret must exist before --restart.
 This script deploys only the bridge files and non-secret systemd drop-in.
@ -36,6 +41,7 @@ USAGE
 for arg in "$@"; do
  case "$arg" in
    --dry-run) DRY_RUN=true ;;
+    --preflight-only) PREFLIGHT_ONLY=true ;;
    --restart) RESTART=true ;;
    --verify-only) VERIFY_ONLY=true ;;
    --help|-h)
@ -50,28 +56,72 @@ for arg in "$@"; do
  esac
 done

-for path in "$WRAPPER_REL" "$TOOL_REL" "$DROPIN_REL"; do
+if $PREFLIGHT_ONLY && $RESTART; then
+  echo "--preflight-only and --restart are mutually exclusive." >&2
+  exit 64
+fi
+if $VERIFY_ONLY && { $PREFLIGHT_ONLY || $RESTART; }; then
+  echo "--verify-only cannot be combined with --preflight-only or --restart." >&2
+  exit 64
+fi
+
+for path in \
+  "$WRAPPER_REL" \
+  "$TOOL_REL" \
+  "$PERMISSION_VERIFIER_REL" \
+  "$SERVICE_ENV_VERIFIER_REL" \
+  "$DROPIN_REL"; do
  if [ ! -f "$REPO_ROOT/$path" ]; then
    echo "Required source file is missing: $path" >&2
    exit 66
  fi
+  if [ -L "$REPO_ROOT/$path" ]; then
+    echo "Refusing symlinked runtime source file: $path" >&2
+    exit 65
+  fi
 done

 if ! grep -Fxq 'UnsetEnvironment=PGPASSWORD' "$REPO_ROOT/$DROPIN_REL"; then
  echo "Runtime drop-in must explicitly unset inherited PGPASSWORD." >&2
  exit 65
 fi
-if ! grep -Fxq "Environment=CLOUDSDK_CONFIG=$REMOTE_CLOUDSDK_CONFIG" "$REPO_ROOT/$DROPIN_REL"; then
-  echo "Runtime drop-in CLOUDSDK_CONFIG does not match $REMOTE_CLOUDSDK_CONFIG." >&2
+if ! grep -Fxq 'Environment=TELEO_GCP_METADATA_ONLY=1' "$REPO_ROOT/$DROPIN_REL"; then
+  echo "Runtime drop-in must enforce metadata-only GCP credentials." >&2
+  exit 65
+fi
+if ! grep -Fxq "BindReadOnlyPaths=$REMOTE_RUNTIME_BIN:$SERVICE_PROFILE_BIN" "$REPO_ROOT/$DROPIN_REL"; then
+  echo "Runtime drop-in does not bind the root-controlled runtime into the service profile." >&2
+  exit 65
+fi
+if ! grep -Fxq "ReadOnlyPaths=$SERVICE_HERMES_ROOT" "$REPO_ROOT/$DROPIN_REL"; then
+  echo "Runtime drop-in does not protect the service-profile ancestor from replacement." >&2
+  exit 65
+fi
+if ! grep -Fxq "ReadWritePaths=$SERVICE_PROFILE_ROOT/state $SERVICE_PROFILE_ROOT/workspace" "$REPO_ROOT/$DROPIN_REL"; then
+  echo "Runtime drop-in does not limit service-profile writes to state and workspace." >&2
+  exit 65
+fi
+if ! grep -Fxq 'CapabilityBoundingSet=~CAP_SYS_ADMIN' "$REPO_ROOT/$DROPIN_REL"; then
+  echo "Runtime drop-in must remove CAP_SYS_ADMIN from the service." >&2
  exit 65
 fi

 SOURCE_REVISION="$(git -C "$REPO_ROOT" rev-parse HEAD)"
-if ! git -C "$REPO_ROOT" diff --quiet HEAD -- "$WRAPPER_REL" "$TOOL_REL" "$DROPIN_REL"; then
+if ! git -C "$REPO_ROOT" diff --quiet HEAD -- \
+  "$WRAPPER_REL" \
+  "$TOOL_REL" \
+  "$PERMISSION_VERIFIER_REL" \
+  "$SERVICE_ENV_VERIFIER_REL" \
+  "$DROPIN_REL"; then
  echo "Refusing to deploy runtime files that do not match HEAD." >&2
  exit 65
 fi
-if [ -n "$(git -C "$REPO_ROOT" ls-files --others --exclude-standard -- "$WRAPPER_REL" "$TOOL_REL" "$DROPIN_REL")" ]; then
+if [ -n "$(git -C "$REPO_ROOT" ls-files --others --exclude-standard -- \
+  "$WRAPPER_REL" \
+  "$TOOL_REL" \
+  "$PERMISSION_VERIFIER_REL" \
+  "$SERVICE_ENV_VERIFIER_REL" \
+  "$DROPIN_REL")" ]; then
  echo "Refusing to deploy untracked runtime files." >&2
  exit 65
 fi
@ -85,6 +135,8 @@ if ! git -C "$REPO_ROOT" merge-base --is-ancestor "$SOURCE_REVISION" "$MERGED_RE
 fi
 WRAPPER_SHA="$(shasum -a 256 "$REPO_ROOT/$WRAPPER_REL" | awk '{print $1}')"
 TOOL_SHA="$(shasum -a 256 "$REPO_ROOT/$TOOL_REL" | awk '{print $1}')"
+PERMISSION_VERIFIER_SHA="$(shasum -a 256 "$REPO_ROOT/$PERMISSION_VERIFIER_REL" | awk '{print $1}')"
+SERVICE_ENV_VERIFIER_SHA="$(shasum -a 256 "$REPO_ROOT/$SERVICE_ENV_VERIFIER_REL" | awk '{print $1}')"
 DROPIN_SHA="$(shasum -a 256 "$REPO_ROOT/$DROPIN_REL" | awk '{print $1}')"

 GCP_SSH=(
@ -123,64 +175,132 @@ assert_service_running() {
  fi
 }

-assert_runtime_environment() {
-  local environment runtime_dir_state
-  environment="$(systemctl show "$SERVICE" --property=Environment --value)"
-  case " $environment " in
-    *" PGPASSWORD="*)
-      echo "Service environment still contains PGPASSWORD." >&2
+assert_unit_configuration() {
+  local require_reviewed="${1:-true}"
+  local dropin_path dropin_name dropin_paths environment_files reviewed_dropin_seen=false
+  dropin_paths="$(systemctl show "$SERVICE" --property=DropInPaths --value)"
+  environment_files="$(systemctl show "$SERVICE" --property=EnvironmentFiles --value)"
+  if [ -n "$environment_files" ]; then
+    echo "Service has an effective EnvironmentFile, which is not allowed for the scoped runtime." >&2
+    return 1
+  fi
+  for dropin_path in $dropin_paths; do
+    if [ "$dropin_path" = "$REMOTE_DROPIN_DIR/$DROPIN_NAME" ]; then
+      reviewed_dropin_seen=true
+      continue
+    fi
+    dropin_name="${dropin_path##*/}"
+    if [[ "$dropin_name" > "$DROPIN_NAME" ]]; then
+      echo "Service has a later drop-in than the reviewed Cloud SQL configuration: $dropin_name" >&2
      return 1
-      ;;
-  esac
-  case " $environment " in
-    *" CLOUDSDK_CONFIG=$REMOTE_CLOUDSDK_CONFIG "*) ;;
-    *)
-      echo "Service does not use the isolated CLOUDSDK_CONFIG." >&2
-      return 1
-      ;;
-  esac
-  runtime_dir_state="$(stat -c '%U:%G:%a' "$REMOTE_CLOUDSDK_CONFIG")"
-  if [ "$runtime_dir_state" != "teleo:teleo:700" ]; then
-    echo "Isolated CLOUDSDK_CONFIG has unexpected ownership or mode: $runtime_dir_state" >&2
+    fi
+  done
+  if [ "$require_reviewed" = true ] && [ "$reviewed_dropin_seen" != true ]; then
+    echo "Service does not load the reviewed Cloud SQL drop-in." >&2
    return 1
  fi
 }

+assert_runtime_environment() {
+  local verifier_path="$1" require_reviewed="${2:-true}" main_pid
+  main_pid="$(systemctl show "$SERVICE" --property=MainPID --value)"
+  sudo /usr/bin/python3 "$verifier_path" --pid "$main_pid"
+  assert_unit_configuration "$require_reviewed"
+}
+
 assert_attached_service_account() {
-  local sdk_config="$1" metadata_email
-  sudo install -d -o teleo -g teleo -m 0700 "$sdk_config"
+  local metadata_email
  metadata_email="$(
-    sudo -n -u teleo env -u PGPASSWORD \
+    sudo -n -u teleo env -i \
      HOME=/home/teleo \
-      CLOUDSDK_CONFIG="$sdk_config" \
-      curl --fail --silent --show-error \
+      PATH=/usr/local/sbin:/usr/local/bin:/usr/sbin:/usr/bin:/sbin:/bin \
+      /usr/bin/curl -q --noproxy '*' --proto '=http' --max-time 10 --fail --silent --show-error \
        --header 'Metadata-Flavor: Google' \
-        'http://metadata.google.internal/computeMetadata/v1/instance/service-accounts/default/email'
+        'http://169.254.169.254/computeMetadata/v1/instance/service-accounts/default/email'
  )"
  if [ "$metadata_email" != "$EXPECTED_VM_SERVICE_ACCOUNT" ]; then
    echo "Attached VM service account mismatch: $metadata_email" >&2
    return 1
  fi
-
-  # An empty, phase-local Cloud SDK config forces this token request to use
-  # the VM's attached identity instead of an operator's cached credentials.
-  sudo -n -u teleo env -u PGPASSWORD \
-    HOME=/home/teleo \
-    CLOUDSDK_CONFIG="$sdk_config" \
-    CLOUDSDK_CORE_PROJECT="$PROJECT" \
-    gcloud --quiet auth print-access-token >/dev/null
  echo "ATTACHED_VM_SERVICE_ACCOUNT=$metadata_email"
 }

+assert_administrator_secret_denied() {
+  local main_pid
+  main_pid="$(systemctl show "$SERVICE" --property=MainPID --value)"
+  sudo nsenter -t "$main_pid" -m --env -- \
+    /usr/bin/setpriv \
+      --reuid=teleo \
+      --regid=teleo \
+      --init-groups \
+      --no-new-privs \
+      /usr/bin/python3 - "$PROJECT" "$EXPECTED_VM_SERVICE_ACCOUNT" <<'PY'
+import json
+import sys
+import urllib.error
+import urllib.parse
+import urllib.request
+
+project, expected_email = sys.argv[1:]
+metadata_headers = {"Metadata-Flavor": "Google"}
+opener = urllib.request.build_opener(urllib.request.ProxyHandler({}))
+
+
+def metadata(path: str) -> bytes:
+    request = urllib.request.Request(
+        "http://169.254.169.254/computeMetadata/v1/" + path,
+        headers=metadata_headers,
+    )
+    with opener.open(request, timeout=10) as response:
+        return response.read(65536)
+
+
+try:
+    email = metadata("instance/service-accounts/default/email").decode("utf-8").strip()
+    if email != expected_email:
+        raise RuntimeError
+    token_payload = json.loads(metadata("instance/service-accounts/default/token"))
+    token = token_payload.get("access_token")
+    if token_payload.get("token_type") != "Bearer" or not isinstance(token, str) or not token:
+        raise RuntimeError
+    secret = urllib.parse.quote("gcp-teleo-pgvector-standby-postgres-password", safe="")
+    url = f"https://secretmanager.googleapis.com/v1/projects/{project}/secrets/{secret}/versions/latest:access"
+    request = urllib.request.Request(url, headers={"Authorization": f"Bearer {token}"})
+    try:
+        response = opener.open(request, timeout=10)
+    except urllib.error.HTTPError as error:
+        body = error.read(65536)
+        parsed = json.loads(body)
+        detail = parsed.get("error", {})
+        message = str(detail.get("message", "")).lower()
+        if error.code != 403 or detail.get("status") != "PERMISSION_DENIED":
+            raise RuntimeError from None
+        if "secretmanager.versions.access" not in message:
+            raise RuntimeError
+    else:
+        response.close()
+        raise RuntimeError
+except Exception:
+    raise SystemExit("administrator secret was not the exact expected metadata-identity IAM denial") from None
+
+print(json.dumps({
+    "administrator_secret_access": "iam_permission_denied",
+    "credential_context": "systemd_main_pid_environment",
+    "identity_source": "gce_metadata",
+    "stdout_discarded": True,
+}, sort_keys=True))
+PY
+}
+
 run_scoped_status() {
-  local phase="$1" tool_path="$2" sdk_config="$3"
-  assert_attached_service_account "$sdk_config"
+  local phase="$1" tool_path="$2"
+  assert_attached_service_account
  echo "SCOPED_STATUS phase=$phase user=teleo database=teleo_canonical"
-  sudo -n -u teleo env -u PGPASSWORD \
+  sudo -n -u teleo env -i \
    HOME=/home/teleo \
-    CLOUDSDK_CONFIG="$sdk_config" \
-    CLOUDSDK_CORE_PROJECT="$PROJECT" \
+    PATH=/usr/local/sbin:/usr/local/bin:/usr/sbin:/usr/bin:/sbin:/bin \
    TELEO_GCP_PROJECT=teleo-501523 \
+    TELEO_GCP_METADATA_ONLY=1 \
    TELEO_CLOUDSQL_HOST=10.61.0.3 \
    TELEO_CLOUDSQL_PORT=5432 \
    TELEO_CLOUDSQL_DB=teleo_canonical \
@ -188,46 +308,238 @@ run_scoped_status() {
    TELEO_CLOUDSQL_USER=leoclean_kb_runtime \
    TELEO_CLOUDSQL_PASSWORD_SECRET=gcp-teleo-pgvector-standby-leoclean-kb-runtime-password \
    TELEO_CLOUDSQL_ENABLE_AUDIT_FALLBACK=0 \
-    python3 "$tool_path" status --format json --redacted
+    /usr/bin/python3 "$tool_path" status --format json --redacted
+}
+
+run_service_wrapper_status() {
+  local phase="$1" main_pid
+  assert_attached_service_account
+  main_pid="$(systemctl show "$SERVICE" --property=MainPID --value)"
+  echo "SCOPED_WRAPPER_STATUS phase=$phase user=teleo database=teleo_canonical"
+  # --env imports the target MainPID's effective /proc environment. setpriv
+  # drops back to the service's Unix identity without sudo resetting that env.
+  sudo nsenter -t "$main_pid" -m --env -- \
+    /usr/bin/setpriv \
+      --reuid=teleo \
+      --regid=teleo \
+      --init-groups \
+      --no-new-privs \
+      "$SERVICE_PROFILE_BIN/teleo-kb" status --format json --redacted
+}
+
+service_fingerprint() {
+  printf '%s|%s|%s|%s' \
+    "$(systemctl show "$SERVICE" --property=ActiveState --value)" \
+    "$(systemctl show "$SERVICE" --property=SubState --value)" \
+    "$(systemctl show "$SERVICE" --property=MainPID --value)" \
+    "$(systemctl show "$SERVICE" --property=NRestarts --value)"
+}
+
+assert_service_fingerprint() {
+  local expected="$1" actual
+  actual="$(service_fingerprint)"
+  if [ "$actual" != "$expected" ]; then
+    echo "Service state changed during the read-only preflight." >&2
+    return 1
+  fi
+  echo "PREFLIGHT_SERVICE_UNCHANGED fingerprint=$actual"
+}
+
+run_permission_verifier() {
+  local phase="$1" verifier_path="$2" receipt_path="$3" receipt_dir run_id receipt_state
+  run_id="$(date -u +%Y%m%d%H%M%S)-$phase"
+  receipt_dir="$(dirname "$receipt_path")"
+  sudo -n -u teleo mkdir -p -- "$receipt_dir"
+  sudo -n -u teleo chmod 0700 "$receipt_dir"
+  echo "NEGATIVE_PERMISSION_RECEIPT phase=$phase run_id=$run_id"
+  sudo -n -u teleo env -i \
+    HOME=/home/teleo \
+    PATH=/usr/local/sbin:/usr/local/bin:/usr/sbin:/usr/bin:/sbin:/bin \
+    /usr/bin/python3 "$verifier_path" --run-id "$run_id" --output "$receipt_path"
+  receipt_state="$(sudo stat -c '%U:%G:%a' "$receipt_path")"
+  if [ "$receipt_state" != "teleo:teleo:600" ]; then
+    echo "Permission receipt has unexpected ownership or mode: $receipt_state" >&2
+    return 1
+  fi
+  sudo /usr/bin/python3 - "$receipt_path" <<'PY'
+import json
+import sys
+from pathlib import Path
+
+receipt = json.loads(Path(sys.argv[1]).read_text(encoding="utf-8"))
+expected = {
+    "artifact": "gcp_leoclean_runtime_permissions",
+    "current_tier": "T3_live_readonly",
+    "mode": "live_private_gcp_staging",
+    "required_tier": "T3_live_readonly",
+    "status": "pass",
+}
+mismatched = sorted(key for key, value in expected.items() if receipt.get(key) != value)
+if mismatched:
+    raise SystemExit("permission receipt contract mismatch: " + ",".join(mismatched))
+print(json.dumps({"permission_receipt": "validated", "validated_fields": sorted(expected)}, sort_keys=True))
+PY
+}
+
+assert_installed_files() {
+  local wrapper tool permission_verifier service_env_verifier dropin revision executable_dir protected_dir protected_file
+  wrapper="$REMOTE_RUNTIME_BIN/teleo-kb"
+  tool="$REMOTE_RUNTIME_BIN/cloudsql_memory_tool.py"
+  permission_verifier="$REMOTE_RUNTIME_BIN/verify_gcp_leoclean_runtime_permissions.py"
+  service_env_verifier="$REMOTE_RUNTIME_BIN/verify_gcp_leoclean_service_environment.py"
+  dropin="$REMOTE_DROPIN_DIR/$DROPIN_NAME"
+  revision="$REMOTE_RUNTIME_BIN/.livingip-runtime-revision"
+  test "$(sudo sha256sum "$wrapper" | awk '{print $1}')" = "$WRAPPER_SHA"
+  test "$(sudo sha256sum "$tool" | awk '{print $1}')" = "$TOOL_SHA"
+  test "$(sudo sha256sum "$permission_verifier" | awk '{print $1}')" = "$PERMISSION_VERIFIER_SHA"
+  test "$(sudo sha256sum "$service_env_verifier" | awk '{print $1}')" = "$SERVICE_ENV_VERIFIER_SHA"
+  test "$(sudo sha256sum "$dropin" | awk '{print $1}')" = "$DROPIN_SHA"
+  test "$(sudo stat -c '%U:%G:%a' "$REMOTE_RUNTIME_BIN")" = "root:root:755"
+  test "$(sudo stat -c '%U:%G:%a' "$wrapper")" = "root:root:755"
+  test "$(sudo stat -c '%U:%G:%a' "$tool")" = "root:root:755"
+  test "$(sudo stat -c '%U:%G:%a' "$permission_verifier")" = "root:root:755"
+  test "$(sudo stat -c '%U:%G:%a' "$service_env_verifier")" = "root:root:755"
+  test "$(sudo stat -c '%U:%G:%a' "$revision")" = "root:root:644"
+  test "$(sudo stat -c '%U:%G:%a' "$dropin")" = "root:root:644"
+  test "$(sudo cat "$revision")" = "$SOURCE_REVISION"
+  for protected_dir in \
+    /usr \
+    /usr/local \
+    /usr/local/libexec \
+    /usr/local/libexec/livingip \
+    "$REMOTE_RUNTIME_BIN" \
+    "$REMOTE_DROPIN_DIR"; do
+    sudo test -d "$protected_dir"
+    sudo test ! -L "$protected_dir"
+    test "$(sudo stat -c '%U:%G' "$protected_dir")" = "root:root"
+    sudo -n -u teleo test ! -w "$protected_dir"
+  done
+  for protected_file in \
+    "$wrapper" \
+    "$tool" \
+    "$permission_verifier" \
+    "$service_env_verifier" \
+    "$revision" \
+    "$dropin"; do
+    sudo test -f "$protected_file"
+    sudo test ! -L "$protected_file"
+    sudo -n -u teleo test ! -w "$protected_file"
+  done
+  for executable_dir in \
+    /usr/local/sbin \
+    /usr/local/bin \
+    /usr/sbin \
+    /usr/bin \
+    /sbin \
+    /bin; do
+    sudo test -d "$executable_dir"
+    test "$(sudo stat -Lc '%U:%G' "$executable_dir")" = "root:root"
+    sudo -n -u teleo test ! -w "$executable_dir"
+  done
+  for protected_file in /bin/bash /usr/bin/curl /usr/bin/python3; do
+    sudo test -x "$protected_file"
+    test "$(sudo stat -Lc '%U:%G' "$protected_file")" = "root:root"
+    sudo -n -u teleo test ! -w "$protected_file"
+  done
+  sudo grep -Fx 'UnsetEnvironment=PGPASSWORD' "$dropin"
+  sudo grep -E '^Environment=TELEO_(KB_MODE|GCP_PROJECT|GCP_METADATA_ONLY|CLOUDSQL_|CANONICAL_CLOUDSQL_DB)' "$dropin"
+  sudo grep -Fx "ReadOnlyPaths=$SERVICE_HERMES_ROOT" "$dropin"
+  sudo grep -Fx "ReadWritePaths=$SERVICE_PROFILE_ROOT/state $SERVICE_PROFILE_ROOT/workspace" "$dropin"
+  sudo grep -Fx "BindReadOnlyPaths=$REMOTE_RUNTIME_BIN:$SERVICE_PROFILE_BIN" "$dropin"
+  sudo grep -Fx 'CapabilityBoundingSet=~CAP_SYS_ADMIN' "$dropin"
 }

 assert_deployed_files() {
-  local wrapper tool dropin
-  wrapper="$REMOTE_PROFILE_BIN/teleo-kb"
-  tool="$REMOTE_PROFILE_BIN/cloudsql_memory_tool.py"
-  dropin="$REMOTE_DROPIN_DIR/$DROPIN_NAME"
-  test "$(sha256sum "$wrapper" | awk '{print $1}')" = "$WRAPPER_SHA"
-  test "$(sha256sum "$tool" | awk '{print $1}')" = "$TOOL_SHA"
-  test "$(sudo sha256sum "$dropin" | awk '{print $1}')" = "$DROPIN_SHA"
-  sudo grep -Fx 'UnsetEnvironment=PGPASSWORD' "$dropin"
-  sudo grep -E '^Environment=(CLOUDSDK_CONFIG|TELEO_(KB_MODE|GCP_PROJECT|CLOUDSQL_|CANONICAL_CLOUDSQL_DB))' "$dropin"
+  local main_pid namespace_state source_state mount_state
+  local hermes_mount_state state_mount_state workspace_mount_state capability_set
+  assert_installed_files
+
+  main_pid="$(systemctl show "$SERVICE" --property=MainPID --value)"
+  source_state="$(stat -Lc '%d:%i' "$REMOTE_RUNTIME_BIN")"
+  namespace_state="$(sudo nsenter -t "$main_pid" -m -- stat -Lc '%d:%i' "$SERVICE_PROFILE_BIN")"
+  if [ "$namespace_state" != "$source_state" ]; then
+    echo "Service namespace does not bind the reviewed runtime directory." >&2
+    return 1
+  fi
+  mount_state="$(sudo nsenter -t "$main_pid" -m -- findmnt -T "$SERVICE_PROFILE_BIN" -n -o OPTIONS)"
+  case ",$mount_state," in
+    *,ro,*) ;;
+    *)
+      echo "Service runtime bind is not read-only." >&2
+      return 1
+      ;;
+  esac
+  hermes_mount_state="$(sudo nsenter -t "$main_pid" -m -- findmnt -M "$SERVICE_HERMES_ROOT" -n -o OPTIONS)"
+  state_mount_state="$(sudo nsenter -t "$main_pid" -m -- findmnt -M "$SERVICE_PROFILE_ROOT/state" -n -o OPTIONS)"
+  workspace_mount_state="$(sudo nsenter -t "$main_pid" -m -- findmnt -M "$SERVICE_PROFILE_ROOT/workspace" -n -o OPTIONS)"
+  case ",$hermes_mount_state," in
+    *,ro,*) ;;
+    *)
+      echo "Service .hermes ancestor mount is not read-only." >&2
+      return 1
+      ;;
+  esac
+  case ",$state_mount_state," in
+    *,rw,*) ;;
+    *)
+      echo "Service state mount is not writable." >&2
+      return 1
+      ;;
+  esac
+  case ",$workspace_mount_state," in
+    *,rw,*) ;;
+    *)
+      echo "Service workspace mount is not writable." >&2
+      return 1
+      ;;
+  esac
+  sudo nsenter -t "$main_pid" -m -- /usr/bin/sudo -n -u teleo test ! -w /home
+  sudo nsenter -t "$main_pid" -m -- /usr/bin/sudo -n -u teleo test ! -w "$SERVICE_HERMES_ROOT"
+  sudo nsenter -t "$main_pid" -m -- /usr/bin/sudo -n -u teleo test ! -w "$SERVICE_HERMES_ROOT/profiles"
+  sudo nsenter -t "$main_pid" -m -- /usr/bin/sudo -n -u teleo test ! -w "$SERVICE_PROFILE_ROOT"
+  sudo nsenter -t "$main_pid" -m -- /usr/bin/sudo -n -u teleo test ! -w "$SERVICE_PROFILE_BIN"
+  sudo nsenter -t "$main_pid" -m -- /usr/bin/sudo -n -u teleo test -w "$SERVICE_PROFILE_ROOT/state"
+  sudo nsenter -t "$main_pid" -m -- /usr/bin/sudo -n -u teleo test -w "$SERVICE_PROFILE_ROOT/workspace"
+  capability_set="$(systemctl show "$SERVICE" --property=CapabilityBoundingSet --value)"
+  if printf '%s\n' "$capability_set" | grep -Eqi '(^|[[:space:]])cap_sys_admin([[:space:]]|$)'; then
+    echo "Service capability bounding set still contains CAP_SYS_ADMIN." >&2
+    return 1
+  fi
+  test "$(sudo nsenter -t "$main_pid" -m -- sha256sum "$SERVICE_PROFILE_BIN/teleo-kb" | awk '{print $1}')" = "$WRAPPER_SHA"
+  test "$(sudo nsenter -t "$main_pid" -m -- sha256sum "$SERVICE_PROFILE_BIN/cloudsql_memory_tool.py" | awk '{print $1}')" = "$TOOL_SHA"
+  test "$(sudo nsenter -t "$main_pid" -m -- sha256sum "$SERVICE_PROFILE_BIN/verify_gcp_leoclean_runtime_permissions.py" | awk '{print $1}')" = "$PERMISSION_VERIFIER_SHA"
+  test "$(sudo nsenter -t "$main_pid" -m -- sha256sum "$SERVICE_PROFILE_BIN/verify_gcp_leoclean_service_environment.py" | awk '{print $1}')" = "$SERVICE_ENV_VERIFIER_SHA"
 }
 REMOTE
 )

 printf -v verify_context \
-  'PROJECT=%q\nSERVICE=%q\nEXPECTED_VM_SERVICE_ACCOUNT=%q\nREMOTE_PROFILE_BIN=%q\nREMOTE_DROPIN_DIR=%q\nREMOTE_CLOUDSDK_CONFIG=%q\nDROPIN_NAME=%q\nWRAPPER_SHA=%q\nTOOL_SHA=%q\nDROPIN_SHA=%q\n' \
-  "$PROJECT" "$SERVICE" "$EXPECTED_VM_SERVICE_ACCOUNT" "$REMOTE_PROFILE_BIN" \
-  "$REMOTE_DROPIN_DIR" "$REMOTE_CLOUDSDK_CONFIG" "$DROPIN_NAME" \
-  "$WRAPPER_SHA" "$TOOL_SHA" "$DROPIN_SHA"
+  'PROJECT=%q\nSERVICE=%q\nEXPECTED_VM_SERVICE_ACCOUNT=%q\nREMOTE_RUNTIME_BIN=%q\nSERVICE_PROFILE_BIN=%q\nSERVICE_PROFILE_ROOT=%q\nSERVICE_HERMES_ROOT=%q\nREMOTE_DROPIN_DIR=%q\nDROPIN_NAME=%q\nWRAPPER_SHA=%q\nTOOL_SHA=%q\nPERMISSION_VERIFIER_SHA=%q\nSERVICE_ENV_VERIFIER_SHA=%q\nDROPIN_SHA=%q\nSOURCE_REVISION=%q\n' \
+  "$PROJECT" "$SERVICE" "$EXPECTED_VM_SERVICE_ACCOUNT" "$REMOTE_RUNTIME_BIN" "$SERVICE_PROFILE_BIN" "$SERVICE_PROFILE_ROOT" "$SERVICE_HERMES_ROOT" \
+  "$REMOTE_DROPIN_DIR" "$DROPIN_NAME" \
+  "$WRAPPER_SHA" "$TOOL_SHA" "$PERMISSION_VERIFIER_SHA" "$SERVICE_ENV_VERIFIER_SHA" "$DROPIN_SHA" "$SOURCE_REVISION"

 verify_body=$(cat <<'REMOTE'
 set -euo pipefail
 verification_tmp="$(mktemp -d /tmp/teleo-gcp-runtime-verify.XXXXXX)"
+sudo chown teleo:teleo "$verification_tmp"
+sudo chmod 0700 "$verification_tmp"
 cleanup_verification() { sudo rm -rf -- "$verification_tmp"; }
 trap cleanup_verification EXIT
 assert_deployed_files
 assert_service_running
-assert_runtime_environment
-run_scoped_status verify "$REMOTE_PROFILE_BIN/cloudsql_memory_tool.py" "$verification_tmp/gcloud"
+assert_runtime_environment "$REMOTE_RUNTIME_BIN/verify_gcp_leoclean_service_environment.py"
+run_service_wrapper_status verify
+assert_administrator_secret_denied
+run_permission_verifier verify "$REMOTE_RUNTIME_BIN/verify_gcp_leoclean_runtime_permissions.py" "$verification_tmp/permission-receipt.json"
 systemctl show "$SERVICE" -p ActiveState -p SubState -p NRestarts -p MainPID -p User --no-pager
 REMOTE
 )
 verify_command="${verify_context}${remote_helpers}"$'\n'"${verify_body}"

 if $DRY_RUN; then
-  echo "DRY RUN: project=$PROJECT zone=$ZONE instance=$INSTANCE service=$SERVICE restart=$RESTART"
-  echo "DRY RUN: revision=$SOURCE_REVISION wrapper_sha256=$WRAPPER_SHA tool_sha256=$TOOL_SHA dropin_sha256=$DROPIN_SHA"
+  echo "DRY RUN: project=$PROJECT zone=$ZONE instance=$INSTANCE service=$SERVICE preflight_only=$PREFLIGHT_ONLY restart=$RESTART"
+  echo "DRY RUN: revision=$SOURCE_REVISION wrapper_sha256=$WRAPPER_SHA tool_sha256=$TOOL_SHA permission_verifier_sha256=$PERMISSION_VERIFIER_SHA service_env_verifier_sha256=$SERVICE_ENV_VERIFIER_SHA dropin_sha256=$DROPIN_SHA"
  exit 0
 fi

@ -236,39 +548,88 @@ if $VERIFY_ONLY; then
  exit 0
 fi

-if ! $RESTART; then
-  echo "Refusing to install runtime files without --restart; use --dry-run or --verify-only for read-only work." >&2
+if ! $RESTART && ! $PREFLIGHT_ONLY; then
+  echo "Refusing to install runtime files without --restart; use --dry-run, --preflight-only, or --verify-only for read-only work." >&2
  exit 64
 fi

-REMOTE_TMP="/tmp/teleo-gcp-leoclean-runtime-$(date -u +%Y%m%dT%H%M%SZ)-$$"
 printf -v sync_context \
-  'PROJECT=%q\nSERVICE=%q\nEXPECTED_VM_SERVICE_ACCOUNT=%q\nREMOTE_PROFILE_BIN=%q\nREMOTE_DROPIN_DIR=%q\nREMOTE_CLOUDSDK_CONFIG=%q\nDROPIN_NAME=%q\nWRAPPER_SHA=%q\nTOOL_SHA=%q\nDROPIN_SHA=%q\nREMOTE_TMP=%q\nWRAPPER_REL=%q\nTOOL_REL=%q\nDROPIN_REL=%q\nSOURCE_REVISION=%q\n' \
-  "$PROJECT" "$SERVICE" "$EXPECTED_VM_SERVICE_ACCOUNT" "$REMOTE_PROFILE_BIN" \
-  "$REMOTE_DROPIN_DIR" "$REMOTE_CLOUDSDK_CONFIG" "$DROPIN_NAME" \
-  "$WRAPPER_SHA" "$TOOL_SHA" "$DROPIN_SHA" "$REMOTE_TMP" \
-  "$WRAPPER_REL" "$TOOL_REL" "$DROPIN_REL" "$SOURCE_REVISION"
+  'PROJECT=%q\nSERVICE=%q\nEXPECTED_VM_SERVICE_ACCOUNT=%q\nREMOTE_RUNTIME_BIN=%q\nSERVICE_PROFILE_BIN=%q\nSERVICE_PROFILE_ROOT=%q\nSERVICE_HERMES_ROOT=%q\nREMOTE_DROPIN_DIR=%q\nDROPIN_NAME=%q\nWRAPPER_SHA=%q\nTOOL_SHA=%q\nPERMISSION_VERIFIER_SHA=%q\nSERVICE_ENV_VERIFIER_SHA=%q\nDROPIN_SHA=%q\nWRAPPER_REL=%q\nTOOL_REL=%q\nPERMISSION_VERIFIER_REL=%q\nSERVICE_ENV_VERIFIER_REL=%q\nDROPIN_REL=%q\nSOURCE_REVISION=%q\nPREFLIGHT_ONLY=%q\n' \
+  "$PROJECT" "$SERVICE" "$EXPECTED_VM_SERVICE_ACCOUNT" "$REMOTE_RUNTIME_BIN" "$SERVICE_PROFILE_BIN" "$SERVICE_PROFILE_ROOT" "$SERVICE_HERMES_ROOT" \
+  "$REMOTE_DROPIN_DIR" "$DROPIN_NAME" \
+  "$WRAPPER_SHA" "$TOOL_SHA" "$PERMISSION_VERIFIER_SHA" "$SERVICE_ENV_VERIFIER_SHA" "$DROPIN_SHA" \
+  "$WRAPPER_REL" "$TOOL_REL" "$PERMISSION_VERIFIER_REL" "$SERVICE_ENV_VERIFIER_REL" "$DROPIN_REL" "$SOURCE_REVISION" "$PREFLIGHT_ONLY"

 sync_body=$(cat <<'REMOTE'
 set -euo pipefail
-remote_tmp="$REMOTE_TMP"
-profile_bin="$REMOTE_PROFILE_BIN"
+remote_tmp="$(sudo mktemp -d /var/tmp/teleo-gcp-leoclean-runtime.XXXXXX)"
+runtime_bin="$REMOTE_RUNTIME_BIN"
+runtime_parent="$(dirname "$runtime_bin")"
+runtime_grandparent="$(dirname "$runtime_parent")"
+runtime_anchor="$(dirname "$runtime_grandparent")"
 dropin_dir="$REMOTE_DROPIN_DIR"
+dropin_parent="$(dirname "$dropin_dir")"
+payload_dir="$remote_tmp/payload"
 backup_dir="$remote_tmp/backup"
+work_dir="$remote_tmp/work"
+wrapper_stage="$runtime_bin/.teleo-kb.livingip-new.$$"
+tool_stage="$runtime_bin/.cloudsql-memory-tool.livingip-new.$$"
+permission_verifier_stage="$runtime_bin/.runtime-permission-verifier.livingip-new.$$"
+service_env_verifier_stage="$runtime_bin/.service-environment-verifier.livingip-new.$$"
+revision_stage="$runtime_bin/.livingip-runtime-revision.livingip-new.$$"
 dropin_stage="$dropin_dir/.${DROPIN_NAME}.livingip-new.$$"
 mutation_started=false

+assert_existing_root_directory() {
+  local target="$1"
+  if sudo test -e "$target" || sudo test -L "$target"; then
+    sudo test -d "$target"
+    sudo test ! -L "$target"
+    test "$(sudo stat -c '%U:%G' "$target")" = "root:root"
+    sudo -n -u teleo test ! -w "$target"
+  fi
+}
+
+assert_existing_root_file() {
+  local target="$1"
+  if sudo test -e "$target" || sudo test -L "$target"; then
+    sudo test -f "$target"
+    sudo test ! -L "$target"
+    test "$(sudo stat -c '%U:%G' "$target")" = "root:root"
+    sudo -n -u teleo test ! -w "$target"
+  fi
+}
+
 backup_path() {
  local target="$1" name="$2"
  if sudo test -e "$target"; then
    sudo cp -a -- "$target" "$backup_dir/$name"
-    touch "$backup_dir/$name.present"
+    sudo touch "$backup_dir/$name.present"
+  fi
+}
+
+backup_directory_state() {
+  local target="$1" name="$2"
+  if sudo test -d "$target"; then
+    sudo stat -c '%u %g %a' "$target" | sudo tee "$backup_dir/$name.metadata" >/dev/null
+    sudo touch "$backup_dir/$name.present"
+  fi
+}
+
+restore_directory_state() {
+  local target="$1" name="$2" uid gid mode
+  if sudo test -f "$backup_dir/$name.present"; then
+    read -r uid gid mode <<<"$(sudo cat "$backup_dir/$name.metadata")"
+    sudo chown "$uid:$gid" "$target"
+    sudo chmod "$mode" "$target"
+  elif sudo test -d "$target"; then
+    sudo rmdir -- "$target"
  fi
 }

 restore_path() {
  local target="$1" name="$2" restore_rc=0 restore_tmp
-  if [ -f "$backup_dir/$name.present" ]; then
+  if sudo test -f "$backup_dir/$name.present"; then
    restore_tmp="${target}.livingip-rollback.$$"
    sudo rm -f -- "$restore_tmp" || restore_rc=1
    if sudo cp -a -- "$backup_dir/$name" "$restore_tmp"; then
@ -283,15 +644,65 @@ restore_path() {
  return "$restore_rc"
 }

+validate_restored_path() {
+  local target="$1" name="$2"
+  if sudo test -f "$backup_dir/$name.present"; then
+    sudo test -f "$target"
+    sudo test ! -L "$target"
+    sudo cmp -s -- "$backup_dir/$name" "$target"
+    test "$(sudo stat -c '%u:%g:%a' "$target")" = \
+      "$(sudo stat -c '%u:%g:%a' "$backup_dir/$name")"
+  else
+    sudo test ! -e "$target"
+    sudo test ! -L "$target"
+  fi
+}
+
+validate_restored_directory() {
+  local target="$1" name="$2" expected_state
+  if sudo test -f "$backup_dir/$name.present"; then
+    expected_state="$(sudo cat "$backup_dir/$name.metadata" | tr ' ' ':')"
+    sudo test -d "$target"
+    sudo test ! -L "$target"
+    test "$(sudo stat -c '%u:%g:%a' "$target")" = "$expected_state"
+  else
+    sudo test ! -e "$target"
+    sudo test ! -L "$target"
+  fi
+}
+
 rollback_runtime() {
  local rollback_rc=0
  echo "Deployment failed; restoring the complete previous runtime set." >&2
  sudo systemctl stop "$SERVICE" || rollback_rc=1
-  restore_path "$profile_bin/teleo-kb" wrapper || rollback_rc=1
-  restore_path "$profile_bin/cloudsql_memory_tool.py" tool || rollback_rc=1
+  restore_path "$runtime_bin/teleo-kb" wrapper || rollback_rc=1
+  restore_path "$runtime_bin/cloudsql_memory_tool.py" tool || rollback_rc=1
+  restore_path "$runtime_bin/verify_gcp_leoclean_runtime_permissions.py" verifier || rollback_rc=1
+  restore_path "$runtime_bin/verify_gcp_leoclean_service_environment.py" service_env_verifier || rollback_rc=1
  restore_path "$dropin_dir/$DROPIN_NAME" dropin || rollback_rc=1
-  restore_path "$profile_bin/.livingip-runtime-revision" revision || rollback_rc=1
-  sudo systemctl daemon-reload || rollback_rc=1
+  restore_path "$runtime_bin/.livingip-runtime-revision" revision || rollback_rc=1
+  restore_directory_state "$runtime_bin" runtime_bin || rollback_rc=1
+  restore_directory_state "$runtime_parent" runtime_parent || rollback_rc=1
+  restore_directory_state "$runtime_grandparent" runtime_grandparent || rollback_rc=1
+  restore_directory_state "$dropin_dir" dropin_dir || rollback_rc=1
+  if [ "$rollback_rc" -eq 0 ]; then
+    validate_restored_path "$runtime_bin/teleo-kb" wrapper || rollback_rc=1
+    validate_restored_path "$runtime_bin/cloudsql_memory_tool.py" tool || rollback_rc=1
+    validate_restored_path "$runtime_bin/verify_gcp_leoclean_runtime_permissions.py" verifier || rollback_rc=1
+    validate_restored_path "$runtime_bin/verify_gcp_leoclean_service_environment.py" service_env_verifier || rollback_rc=1
+    validate_restored_path "$dropin_dir/$DROPIN_NAME" dropin || rollback_rc=1
+    validate_restored_path "$runtime_bin/.livingip-runtime-revision" revision || rollback_rc=1
+    validate_restored_directory "$runtime_grandparent" runtime_grandparent || rollback_rc=1
+    validate_restored_directory "$runtime_parent" runtime_parent || rollback_rc=1
+    validate_restored_directory "$runtime_bin" runtime_bin || rollback_rc=1
+    validate_restored_directory "$dropin_dir" dropin_dir || rollback_rc=1
+  fi
+  if [ "$rollback_rc" -eq 0 ]; then
+    sudo systemctl daemon-reload || rollback_rc=1
+  fi
+  if [ "$rollback_rc" -eq 0 ]; then
+    assert_unit_configuration false || rollback_rc=1
+  fi
  if [ "$rollback_rc" -eq 0 ]; then
    sudo systemctl start "$SERVICE" || rollback_rc=1
    assert_service_running || rollback_rc=1
@ -312,7 +723,13 @@ on_exit() {
      rc=1
    fi
  fi
-  sudo rm -f -- "$dropin_stage" || true
+  sudo rm -f -- \
+    "$wrapper_stage" \
+    "$tool_stage" \
+    "$permission_verifier_stage" \
+    "$service_env_verifier_stage" \
+    "$revision_stage" \
+    "$dropin_stage" || true
  sudo rm -rf -- "$remote_tmp" || true
  exit "$rc"
 }
@ -321,36 +738,117 @@ trap 'on_exit $?' EXIT
 trap 'exit 130' INT
 trap 'exit 143' TERM

-sudo rm -rf -- "$remote_tmp"
-mkdir -p "$backup_dir"
-tar -C "$remote_tmp" -xf -
+sudo chmod 0711 "$remote_tmp"
+sudo install -d -o root -g root -m 0755 "$payload_dir"
+sudo install -d -o root -g root -m 0700 "$backup_dir"
+sudo install -d -o teleo -g teleo -m 0700 "$work_dir"
+sudo tar --no-same-owner --no-same-permissions --no-xattrs --no-acls --no-selinux -C "$payload_dir" -xf -
+if sudo find "$payload_dir" -type l -print -quit | grep -q .; then
+  echo "Staged runtime payload contains a symlink." >&2
+  exit 65
+fi
+if sudo find "$payload_dir" ! -type d ! -type f -print -quit | grep -q .; then
+  echo "Staged runtime payload contains a non-regular entry." >&2
+  exit 65
+fi
+sudo chown -R root:root "$payload_dir"
+sudo find "$payload_dir" -type d -exec chmod 0555 {} +
+sudo find "$payload_dir" -type f -exec chmod 0444 {} +
+sudo chmod 0555 \
+  "$payload_dir/$WRAPPER_REL" \
+  "$payload_dir/$TOOL_REL" \
+  "$payload_dir/$PERMISSION_VERIFIER_REL" \
+  "$payload_dir/$SERVICE_ENV_VERIFIER_REL"
+test "$(sudo sha256sum "$payload_dir/$WRAPPER_REL" | awk '{print $1}')" = "$WRAPPER_SHA"
+test "$(sudo sha256sum "$payload_dir/$TOOL_REL" | awk '{print $1}')" = "$TOOL_SHA"
+test "$(sudo sha256sum "$payload_dir/$PERMISSION_VERIFIER_REL" | awk '{print $1}')" = "$PERMISSION_VERIFIER_SHA"
+test "$(sudo sha256sum "$payload_dir/$SERVICE_ENV_VERIFIER_REL" | awk '{print $1}')" = "$SERVICE_ENV_VERIFIER_SHA"
+test "$(sudo sha256sum "$payload_dir/$DROPIN_REL" | awk '{print $1}')" = "$DROPIN_SHA"
+test "$(sudo stat -c '%U:%G:%a' "$remote_tmp")" = "root:root:711"
+test "$(sudo stat -c '%U:%G:%a' "$payload_dir")" = "root:root:555"
+test "$(sudo stat -c '%U:%G:%a' "$backup_dir")" = "root:root:700"
+test "$(sudo stat -c '%U:%G:%a' "$work_dir")" = "teleo:teleo:700"
+sudo -n -u teleo test ! -w "$remote_tmp"
+sudo -n -u teleo test ! -w "$payload_dir"
+sudo -n -u teleo test ! -w "$backup_dir"
+sudo test -d "$runtime_anchor"
+sudo test -d "$dropin_parent"
+sudo test ! -L "$runtime_anchor"
+sudo test ! -L "$dropin_parent"
+test "$(sudo stat -c '%U:%G' "$runtime_anchor")" = "root:root"
+test "$(sudo stat -c '%U:%G' "$dropin_parent")" = "root:root"
+sudo -n -u teleo test ! -w "$runtime_anchor"
+sudo -n -u teleo test ! -w "$dropin_parent"
+for existing_directory in \
+  "$runtime_grandparent" \
+  "$runtime_parent" \
+  "$runtime_bin" \
+  "$dropin_dir"; do
+  assert_existing_root_directory "$existing_directory"
+done
+for existing_file in \
+  "$runtime_bin/teleo-kb" \
+  "$runtime_bin/cloudsql_memory_tool.py" \
+  "$runtime_bin/verify_gcp_leoclean_runtime_permissions.py" \
+  "$runtime_bin/verify_gcp_leoclean_service_environment.py" \
+  "$runtime_bin/.livingip-runtime-revision" \
+  "$dropin_dir/$DROPIN_NAME"; do
+  assert_existing_root_file "$existing_file"
+done

 assert_service_running
-run_scoped_status pre "$remote_tmp/$TOOL_REL" "$remote_tmp/gcloud-pre"
+preflight_service_before="$(service_fingerprint)"
+assert_runtime_environment "$payload_dir/$SERVICE_ENV_VERIFIER_REL" false
+run_scoped_status pre "$payload_dir/$TOOL_REL"
+assert_administrator_secret_denied
+run_permission_verifier pre "$payload_dir/$PERMISSION_VERIFIER_REL" "$work_dir/permission-pre/receipt.json"
+assert_service_fingerprint "$preflight_service_before"
+if [ "$PREFLIGHT_ONLY" = true ]; then
+  systemctl show "$SERVICE" -p ActiveState -p SubState -p NRestarts -p MainPID -p User --no-pager
+  exit 0
+fi

-backup_path "$profile_bin/teleo-kb" wrapper
-backup_path "$profile_bin/cloudsql_memory_tool.py" tool
+backup_path "$runtime_bin/teleo-kb" wrapper
+backup_path "$runtime_bin/cloudsql_memory_tool.py" tool
+backup_path "$runtime_bin/verify_gcp_leoclean_runtime_permissions.py" verifier
+backup_path "$runtime_bin/verify_gcp_leoclean_service_environment.py" service_env_verifier
 backup_path "$dropin_dir/$DROPIN_NAME" dropin
-backup_path "$profile_bin/.livingip-runtime-revision" revision
+backup_path "$runtime_bin/.livingip-runtime-revision" revision
+backup_directory_state "$runtime_parent" runtime_parent
+backup_directory_state "$runtime_grandparent" runtime_grandparent
+backup_directory_state "$runtime_bin" runtime_bin
+backup_directory_state "$dropin_dir" dropin_dir

 mutation_started=true
 sudo systemctl stop "$SERVICE"
-sudo install -d -o teleo -g teleo -m 0755 "$profile_bin"
-sudo install -o teleo -g teleo -m 0755 "$remote_tmp/$WRAPPER_REL" "$profile_bin/teleo-kb"
-sudo install -o teleo -g teleo -m 0755 "$remote_tmp/$TOOL_REL" "$profile_bin/cloudsql_memory_tool.py"
+sudo install -d -o root -g root -m 0755 "$runtime_parent"
+sudo install -d -o root -g root -m 0755 "$runtime_bin"
+sudo install -o root -g root -m 0755 "$payload_dir/$WRAPPER_REL" "$wrapper_stage"
+sudo install -o root -g root -m 0755 "$payload_dir/$TOOL_REL" "$tool_stage"
+sudo install -o root -g root -m 0755 "$payload_dir/$PERMISSION_VERIFIER_REL" "$permission_verifier_stage"
+sudo install -o root -g root -m 0755 "$payload_dir/$SERVICE_ENV_VERIFIER_REL" "$service_env_verifier_stage"
+sudo mv -f -- "$wrapper_stage" "$runtime_bin/teleo-kb"
+sudo mv -f -- "$tool_stage" "$runtime_bin/cloudsql_memory_tool.py"
+sudo mv -f -- "$permission_verifier_stage" "$runtime_bin/verify_gcp_leoclean_runtime_permissions.py"
+sudo mv -f -- "$service_env_verifier_stage" "$runtime_bin/verify_gcp_leoclean_service_environment.py"
 sudo install -d -o root -g root -m 0755 "$dropin_dir"
-sudo install -o root -g root -m 0644 "$remote_tmp/$DROPIN_REL" "$dropin_stage"
+sudo install -o root -g root -m 0644 "$payload_dir/$DROPIN_REL" "$dropin_stage"
 sudo mv -f -- "$dropin_stage" "$dropin_dir/$DROPIN_NAME"
-printf '%s\n' "$SOURCE_REVISION" | sudo tee "$profile_bin/.livingip-runtime-revision" >/dev/null
-sudo chown teleo:teleo "$profile_bin/.livingip-runtime-revision"
-sudo chmod 0644 "$profile_bin/.livingip-runtime-revision"
+printf '%s\n' "$SOURCE_REVISION" | sudo tee "$revision_stage" >/dev/null
+sudo chown root:root "$revision_stage"
+sudo chmod 0644 "$revision_stage"
+sudo mv -f -- "$revision_stage" "$runtime_bin/.livingip-runtime-revision"
+assert_installed_files
 sudo systemctl daemon-reload
+assert_unit_configuration
 sudo systemctl start "$SERVICE"

 assert_deployed_files
 assert_service_running
-assert_runtime_environment
-run_scoped_status post "$profile_bin/cloudsql_memory_tool.py" "$remote_tmp/gcloud-post"
+assert_runtime_environment "$runtime_bin/verify_gcp_leoclean_service_environment.py"
+run_service_wrapper_status post
+assert_administrator_secret_denied
+run_permission_verifier post "$runtime_bin/verify_gcp_leoclean_runtime_permissions.py" "$work_dir/permission-post/receipt.json"
 systemctl show "$SERVICE" -p ActiveState -p SubState -p NRestarts -p MainPID -p User --no-pager
 mutation_started=false
 REMOTE
@ -358,4 +856,8 @@ REMOTE
 sync_command="${sync_context}${remote_helpers}"$'\n'"${sync_body}"

 COPYFILE_DISABLE=1 tar --format=ustar -C "$REPO_ROOT" -cf - \
-  "$WRAPPER_REL" "$TOOL_REL" "$DROPIN_REL" | "${GCP_SSH[@]}" --command="$sync_command"
+  "$WRAPPER_REL" \
+  "$TOOL_REL" \
+  "$PERMISSION_VERIFIER_REL" \
+  "$SERVICE_ENV_VERIFIER_REL" \
+  "$DROPIN_REL" | "${GCP_SSH[@]}" --command="$sync_command"
--- a/docs/gcp-leoclean-runtime-reconciliation.md
+++ b/docs/gcp-leoclean-runtime-reconciliation.md
@ -2,8 +2,9 @@

 ## Scope

-This runbook reconciles PR `#145` with the non-production GCP parallel Leo
-service and removes its dependency on the PostgreSQL administrator credential.
+This runbook reconciles PR `#148`, the least-privilege follow-up to PR `#145`,
+with the non-production GCP parallel Leo service and removes its dependency on
+the PostgreSQL administrator credential.
 It does not promote GCP, change the Telegram destination, copy newer VPS data,
 or make `teleo_canonical` production-authoritative.

@ -31,7 +32,8 @@ IAM or networking.
   commit.
 2. `TELEO_KB_MODE=cloudsql`; missing tools or credentials fail closed.
 3. Canonical zero-hit searches do not consult `teleo_restore` unless an
-   operator explicitly opts in.
+   operator explicitly opts in. The service is pinned to database
+   `teleo_canonical` with `TELEO_CLOUDSQL_ENABLE_AUDIT_FALLBACK=0`.
 4. Leo can read the named canonical tables and stage only a
   `pending_review` proposal through `kb_stage.stage_leoclean_proposal(...)`.
 5. Leo cannot directly insert, update, or delete `public.*` or
@ -55,7 +57,7 @@ required runtime secret has an equivalent secret-level binding.

 ### 2. Merge reviewed repository code

-Run CI on the completed PR `#145` repair before deployment. The deployment
+Run CI on the completed PR `#148` repair before deployment. The deployment
 source must be the resulting merged commit, not a working tree or unmerged
 branch.

@ -73,6 +75,9 @@ private VM path. Supply the new runtime password through
 `TELEO_LEOCLEAN_DB_PASSWORD`; the SQL file does not contain it. The migration:

 - creates or rotates `leoclean_kb_runtime`;
+- keeps `leoclean_kb_runtime` `NOLOGIN` while both the `teleo_canonical` grant
+  phase and the legacy `teleo_kb` denial-verification phase run, and enables
+  `LOGIN` only in the final transaction after both phases pass;
 - creates a dedicated `NOLOGIN` function owner with no role memberships;
 - removes stale table, column, sequence, function, and role-membership grants;
 - grants exact canonical reads;
@ -94,26 +99,116 @@ by a `pg_catalog, pg_temp` search path, schema-qualified relations, a fixed
 The administrator password is used only for this bounded bootstrap. Retain no
 password output.

+`teleo_kb` can still be connectable through its existing `PUBLIC CONNECT`
+grant. That database-wide default is not treated as runtime authority. The
+migration denies the scoped role access to the `teleo_restore` schema, the
+runtime client is pinned to `teleo_canonical`, and audit fallback remains
+disabled with `TELEO_CLOUDSQL_ENABLE_AUDIT_FALLBACK=0`.
+
 ### 5. Preflight and deploy the merged runtime

 From the exact merged checkout, run:

 ```bash
 deploy/sync-gcp-leoclean-runtime.sh --dry-run
+deploy/sync-gcp-leoclean-runtime.sh --preflight-only
 deploy/sync-gcp-leoclean-runtime.sh --restart
 ```

-The deploy script runs a scoped, redacted database status preflight before it
-installs files or restarts the service. It refuses dirty or unmerged runtime
-files and refuses a live install without `--restart`. After preflight it stops
-the parallel service, atomically replaces the existing Cloud SQL systemd
-drop-in, installs the reviewed wrapper and helper, records the Git revision,
-starts the service, and verifies all three file hashes. A failure after mutation
-restores the prior wrapper, helper, drop-in, and revision as one set before the
-old service is restarted.
+`--preflight-only` extracts the candidate helper and permission verifier into a
+root-created, root-owned, non-writable VM payload directory, verifies the actual
+service `MainPID` environment, runs the candidate private Cloud SQL status path,
+and runs the sanitized positive-and-negative permission verifier. A separate
+`teleo`-owned directory holds only sanitized receipts; it never feeds an install
+or rollback. The preflight does not stop or restart the service and does not
+install or replace runtime files. It
+captures `ActiveState`, `SubState`, `MainPID`, and `NRestarts` before and after
+the checks and fails if any value changes. The preflight must pass before
+`--restart` is attempted.
+
+The deploy script refuses dirty, symlinked, or unmerged runtime files and
+refuses a live install without `--restart`. Its payload and rollback backup are
+root-owned and non-writable by `teleo`; existing runtime intermediates and
+targets must be real root-owned, non-writable paths. After preflight it stops
+the parallel service, atomically replaces the existing Cloud SQL systemd drop-in, installs the
+reviewed wrapper, helper, and permission verifier into the root-controlled
+`/usr/local/libexec/livingip/leoclean-kb` directory, records the Git revision,
+and verifies every installed hash, owner, mode, path type, and revision before
+systemd reloads the unit or starts the service. The wrapper uses fixed
+`/bin/bash` and `/usr/bin/python3` interpreters, and every directory on the
+service `PATH` must be root-owned and non-writable by `teleo`. Every ancestor of that
+directory, the directory itself, the wrapper, helper, verifier, and revision
+marker must be non-writable by `teleo`. The systemd service receives that
+directory as a read-only bind at its existing
+`/home/teleo/.hermes/profiles/leoclean/bin` path; verification compares the
+source and service-namespace inode and hashes and proves the mount is read-only.
+To prevent the `teleo` service user from renaming a writable ancestor and
+recreating that absolute path, the service namespace mounts
+`/home/teleo/.hermes` read-only, allows writes back only to the profile's
+`state` and `workspace` subdirectories, and removes `CAP_SYS_ADMIN`. Live
+verification requires `.hermes` and `bin` to be read-only, both allowed
+subdirectories to be writable, `/home` to be non-writable by `teleo`, and the
+effective capability set to exclude `CAP_SYS_ADMIN`.
+
+Preflight, post-restart, and `--verify-only` checks inspect the environment of the actual
+systemd `MainPID` through `/proc/<MainPID>/environ`, rather than trusting the
+configured unit environment alone. A standalone fail-closed verifier requires
+the exact reviewed private target and runtime role, requires
+`TELEO_GCP_METADATA_ONLY=1`, and rejects all PostgreSQL, Cloud SDK, proxy, TLS
+trust, broader Google credential, shell-startup, dynamic-loader, Python-loader,
+and administrator-secret overrides without printing their values. Effective
+`EnvironmentFile` use and drop-ins ordered after the reviewed configuration are
+rejected before restart. This blocks
+pre-wrapper injection through fields such as `BASH_ENV`, any `LD_*`,
+`PYTHONPATH`, `PYTHONHTTPSVERIFY`, or `SSLKEYLOGFILE`. The checks also require
+the reviewed drop-in to appear in `DropInPaths`. The wrapper status probe then
+imports the validated environment from the actual `MainPID` with `nsenter
+--env`, enters its mount namespace, drops to `teleo`, and invokes the bound
+wrapper without reinjecting any database identity setting.
+
+The service runtime bypasses Cloud SDK configuration and credential caches
+entirely. The helper obtains the attached service-account email and a bounded
+access token from the fixed GCE metadata endpoint, requires the exact expected
+service account, and accesses only the named scoped Secret Manager version over
+the fixed HTTPS API. Its URL opener disables proxies. The scoped status read
+and administrator-secret IAM denial are rerun after restart. The denial probe
+imports the actual systemd `MainPID` environment and mount namespace, drops to
+the service's `teleo` identity, and must observe the exact
+`secretmanager.versions.access` permission denial. No token or
+secret value is retained. The status read executes the bound `teleo-kb` wrapper
+from inside the service mount namespace, proving the wrapper and its adjacent
+helper rather than bypassing them with a direct helper invocation. A failure
+after mutation restores the prior runtime/drop-in directory existence and
+metadata, wrapper, helper, both verifiers, drop-in, and revision as one set,
+validates it against the root-only backup, and only then reloads systemd and
+restarts the old service.

 ### 6. Verify positive and negative behavior

+`--preflight-only`, `--restart`, and `--verify-only` run the verifier as the
+`teleo` Unix user. To rerun the installed verifier directly on the VM and
+retain its sanitized JSON receipt, use:
+
+```bash
+receipt_dir="$(mktemp -d /tmp/leoclean-permission-receipt.XXXXXX)"
+sudo chown teleo:teleo "$receipt_dir"
+sudo chmod 0700 "$receipt_dir"
+run_id="$(date -u +%Y%m%d%H%M%S)-manual"
+sudo -n -u teleo env -i HOME=/home/teleo \
+  PATH=/usr/local/sbin:/usr/local/bin:/usr/sbin:/usr/bin:/sbin:/bin \
+  python3 /usr/local/libexec/livingip/leoclean-kb/verify_gcp_leoclean_runtime_permissions.py \
+  --run-id "$run_id" \
+  --output "$receipt_dir/permission-receipt.json"
+sudo stat -c '%U:%G:%a' "$receipt_dir/permission-receipt.json"
+```
+
+The command must exit zero, print the same canonical JSON that it writes, and
+leave the receipt as `teleo:teleo:600`. A passing receipt must report
+`status=pass`, `mode=live_private_gcp_staging`, and both `required_tier` and
+`current_tier` as `T3_live_readonly`. Those values are a receipt contract, not
+a claim that this runbook has already been exercised successfully on the live
+staging VM.
+
 Retain a redacted receipt containing:

 - merged Git commit and deployed file hashes;
@ -122,13 +217,28 @@ Retain a redacted receipt containing:
  configuration;
 - `current_database()` and `current_user` showing
  `teleo_canonical|leoclean_kb_runtime`;
+- private server address `10.61.0.3`, port `5432`, and an active SSL session;
+- exact safe runtime-role attributes and zero membership edges in
+  `pg_auth_members`;
+- zero effective database/schema `CREATE`, persistent ownership, table/column
+  DML, sequence privileges, SELECT outside the exact table allowlist, or
+  executable unexpected `SECURITY DEFINER` functions, plus the exact staging
+  function owner/search-path/ACL contract;
 - a real canonical status/search receipt;
 - a transaction-rolled-back call to `stage_leoclean_proposal(...)` that returns
-  `pending_review`;
- denied direct insert into `kb_stage.kb_proposals`;
- denied canonical `public.*` write;
- denied reviewer/apply security-definer function;
- denied forged proposer identity and denied `SET ROLE` escalation;
+  `pending_review` for canonical proposer `leo`, with zero matching canary rows
+  both before and after the transaction;
+- denied direct insert, update, and delete on `kb_stage.kb_proposals`;
+- denied insert, update, and delete on canonical `public.claims`;
+- denied reviewer/apply security-definer functions;
+- exact function-catalog posture: only the five-argument staging function is
+  executable, the forged six-argument overload is absent, and each expected
+  reviewer/apply function exists but is not executable by the runtime role;
+- unavailable forged-proposer overload and denied `SET ROLE` escalation into
+  the staging owner, reviewer, apply, or administrator roles;
+- denied access to `teleo_restore` even when `teleo_kb` remains connectable;
+- readable scoped runtime secret and an IAM permission denial for the
+  administrator secret, with neither secret value retained;
 - zero Telegram messages and zero committed canary rows.

 ### 7. Remove administrator-secret access
--- a/hermes-agent/leoclean-bin/cloudsql_memory_tool.py
+++ b/hermes-agent/leoclean-bin/cloudsql_memory_tool.py
@ -1,20 +1,24 @@
 #!/usr/bin/env python3
 """Cloud SQL memory and KB-proposal bridge for the GCP leoclean profile.

-Canonical claim/strategy application remains review-gated. Read commands query
-the canonical Teleo KB first, then fall back to the restored `teleo_restore`
-shadow schema in Cloud SQL. Proposal commands write staged review records into
-`kb_stage.kb_proposals`; they do not apply canonical truth directly.
+Canonical claim/strategy application remains review-gated. The production-like
+Leo runtime is pinned to the private canonical Cloud SQL database and never
+falls back to the restored `teleo_restore` shadow schema. Proposal commands
+write staged review records into `kb_stage.kb_proposals`; they do not apply
+canonical truth directly.
 """

 from __future__ import annotations

 import argparse
+import base64
+import binascii
 import hashlib
 import json
 import os
 import re
 import subprocess
+import urllib.request
 from typing import Any

 STOPWORDS = {
@ -76,6 +80,38 @@ DEFAULT_CLAIM_BASE_URL = "https://leo.livingip.xyz"
 RETRIEVAL_RECEIPT_SCHEMA = "livingip.teleoKbRetrievalReceipt.v1"
 RUNTIME_DB_USER = "leoclean_kb_runtime"
 RUNTIME_PASSWORD_SECRET = "gcp-teleo-pgvector-standby-leoclean-kb-runtime-password"
+RUNTIME_GCP_PROJECT = "teleo-501523"
+RUNTIME_CLOUDSQL_HOST = "10.61.0.3"
+RUNTIME_CLOUDSQL_PORT = "5432"
+RUNTIME_CLOUDSQL_DB = "teleo_canonical"
+RUNTIME_SERVICE_ACCOUNT = "sa-teleo-prod-vm@teleo-501523.iam.gserviceaccount.com"
+GCE_METADATA_EMAIL_URL = "http://169.254.169.254/computeMetadata/v1/instance/service-accounts/default/email"
+GCE_METADATA_TOKEN_URL = "http://169.254.169.254/computeMetadata/v1/instance/service-accounts/default/token"
+RUNTIME_SECRET_ACCESS_URL = (
+    "https://secretmanager.googleapis.com/v1/projects/teleo-501523/secrets/"
+    "gcp-teleo-pgvector-standby-leoclean-kb-runtime-password/versions/latest:access"
+)
+METADATA_HEADERS = {"Metadata-Flavor": "Google"}
+HTTP_TIMEOUT_SECONDS = 3.0
+MAX_METADATA_EMAIL_BYTES = 256
+MAX_METADATA_TOKEN_BYTES = 4096
+MAX_SECRET_RESPONSE_BYTES = 8192
+MAX_RUNTIME_SECRET_BYTES = 4096
+RUNTIME_TLS_TRUST_ENVIRONMENT = frozenset(
+    {
+        "CURL_CA_BUNDLE",
+        "PYTHONHTTPSVERIFY",
+        "REQUESTS_CA_BUNDLE",
+        "SSL_CERT_DIR",
+        "SSL_CERT_FILE",
+        "SSLKEYLOGFILE",
+    }
+)
+RUNTIME_PSQL_ENV_BASE = {
+    "PATH": "/usr/bin:/bin",
+    "PGSSLMODE": "require",
+    "PGCONNECT_TIMEOUT": "8",
+}
 CLONE_READ_ONLY_PGOPTIONS = "-c default_transaction_read_only=on"
 RECEIPTED_READ_COMMANDS = frozenset(
    {
@ -93,6 +129,18 @@ RECEIPTED_READ_COMMANDS = frozenset(
 )


+class _RejectRedirectHandler(urllib.request.HTTPRedirectHandler):
+    def redirect_request(self, *_args: Any, **_kwargs: Any) -> None:
+        return None
+
+
+RUNTIME_PROXY_HANDLER = urllib.request.ProxyHandler({})
+RUNTIME_HTTP_OPENER = urllib.request.build_opener(
+    RUNTIME_PROXY_HANDLER,
+    _RejectRedirectHandler(),
+)
+
+
 def parse_args() -> argparse.Namespace:
    parser = argparse.ArgumentParser(description=__doc__)
    parser.add_argument("--host", default=os.environ.get("TELEO_CLOUDSQL_HOST", "10.61.0.3"))
@ -246,8 +294,47 @@ def validate_runtime_connection(args: argparse.Namespace) -> None:
            raise SystemExit(f"Leo runtime requires database user {RUNTIME_DB_USER}.")
        if password_secret != RUNTIME_PASSWORD_SECRET:
            raise SystemExit(f"Leo runtime requires scoped password secret {RUNTIME_PASSWORD_SECRET}.")
-        if "PGPASSWORD" in os.environ:
-            raise SystemExit("Refusing inherited PGPASSWORD in Leo runtime mode.")
+        expected_fields = {
+            "project": RUNTIME_GCP_PROJECT,
+            "host": RUNTIME_CLOUDSQL_HOST,
+            "port": RUNTIME_CLOUDSQL_PORT,
+            "db": RUNTIME_CLOUDSQL_DB,
+            "canonical_db": RUNTIME_CLOUDSQL_DB,
+        }
+        for field, expected in expected_fields.items():
+            actual = str(getattr(args, field, "") or "")
+            if actual != expected:
+                raise SystemExit(f"Leo runtime requires {field}={expected}.")
+        if os.environ.get("TELEO_CLOUDSQL_ENABLE_AUDIT_FALLBACK", "0") != "0":
+            raise SystemExit("Leo runtime requires TELEO_CLOUDSQL_ENABLE_AUDIT_FALLBACK=0.")
+        if os.environ.get("TELEO_GCP_METADATA_ONLY") != "1":
+            raise SystemExit("Leo runtime requires TELEO_GCP_METADATA_ONLY=1.")
+        forbidden_environment = any(
+            normalized_key.startswith("PG")
+            or normalized_key.startswith("CLOUDSDK_")
+            or normalized_key == "GOOGLE_APPLICATION_CREDENTIALS"
+            or normalized_key.startswith("LD_")
+            or normalized_key.startswith("BASH_FUNC_")
+            or (normalized_key.startswith("PYTHON") and normalized_key != "PYTHONUNBUFFERED")
+            or normalized_key in {
+                "BASH_ENV",
+                "BASHOPTS",
+                "CDPATH",
+                "ENV",
+                "GLOBIGNORE",
+                "IFS",
+                "PS4",
+                "SHELLOPTS",
+            }
+            or normalized_key == "PROXY"
+            or normalized_key.endswith("_PROXY")
+            or normalized_key in RUNTIME_TLS_TRUST_ENVIRONMENT
+            for normalized_key in (key.upper() for key in os.environ)
+        )
+        if forbidden_environment:
+            raise SystemExit(
+                "Refusing inherited credential, proxy, TLS, or PostgreSQL environment in Leo runtime mode."
+            )
        return

    if mode != "clone-readonly":
@ -261,8 +348,8 @@ def validate_runtime_connection(args: argparse.Namespace) -> None:
        raise SystemExit("Clone credential mode permits read commands only.")
    if pgoptions != CLONE_READ_ONLY_PGOPTIONS:
        raise SystemExit("Clone credential mode requires server-enforced default_transaction_read_only=on.")
-    if not user or (not password_secret and not os.environ.get("PGPASSWORD")):
-        raise SystemExit("Clone credential mode requires an explicit user and credential source.")
+    if not user or not os.environ.get("PGPASSWORD"):
+        raise SystemExit("Clone credential mode requires an explicit user and inherited test credential.")


 def terms_for(query: str) -> list[str]:
@ -305,48 +392,138 @@ def sql_array(values: list[str], cast: str = "text") -> str:
    return "array[" + ",".join(sql_literal(value) for value in values) + f"]::{cast}[]"


+def _read_http_response(request: urllib.request.Request, *, max_bytes: int, purpose: str) -> bytes:
+    try:
+        with RUNTIME_HTTP_OPENER.open(request, timeout=HTTP_TIMEOUT_SECONDS) as response:
+            if response.getcode() != 200:
+                raise SystemExit(f"{purpose} request failed.")
+            body = response.read(max_bytes + 1)
+    except SystemExit:
+        raise
+    # This is a credential-bearing boundary. Never propagate provider, proxy,
+    # TLS, or test-double exception text because it can contain bearer data.
+    except Exception:
+        raise SystemExit(f"{purpose} request failed.") from None
+    if not isinstance(body, bytes) or len(body) > max_bytes:
+        raise SystemExit(f"{purpose} response was invalid.")
+    return body
+
+
+def _strict_json_object(body: bytes, *, purpose: str) -> dict[str, Any]:
+    def reject_duplicate_keys(pairs: list[tuple[str, Any]]) -> dict[str, Any]:
+        value: dict[str, Any] = {}
+        for key, item in pairs:
+            if key in value:
+                raise ValueError("duplicate JSON key")
+            value[key] = item
+        return value
+
+    try:
+        decoded = body.decode("utf-8", errors="strict")
+        value = json.loads(
+            decoded,
+            object_pairs_hook=reject_duplicate_keys,
+            parse_constant=lambda _constant: (_ for _ in ()).throw(ValueError("non-finite JSON value")),
+        )
+    except (UnicodeDecodeError, ValueError, TypeError):
+        raise SystemExit(f"{purpose} response was invalid.") from None
+    if not isinstance(value, dict):
+        raise SystemExit(f"{purpose} response was invalid.")
+    return value
+
+
+def _metadata_request(url: str, *, max_bytes: int, purpose: str) -> bytes:
+    request = urllib.request.Request(url, headers=METADATA_HEADERS, method="GET")
+    return _read_http_response(request, max_bytes=max_bytes, purpose=purpose)
+
+
+def runtime_password_from_metadata() -> str:
+    email_body = _metadata_request(
+        GCE_METADATA_EMAIL_URL,
+        max_bytes=MAX_METADATA_EMAIL_BYTES,
+        purpose="Runtime metadata identity",
+    )
+    try:
+        service_account = email_body.decode("ascii", errors="strict")
+    except UnicodeDecodeError:
+        raise SystemExit("Runtime metadata identity response was invalid.") from None
+    if service_account != RUNTIME_SERVICE_ACCOUNT:
+        raise SystemExit("Runtime metadata identity did not match the required service account.")
+
+    token_value = _strict_json_object(
+        _metadata_request(
+            GCE_METADATA_TOKEN_URL,
+            max_bytes=MAX_METADATA_TOKEN_BYTES,
+            purpose="Runtime metadata token",
+        ),
+        purpose="Runtime metadata token",
+    )
+    access_token = token_value.get("access_token")
+    token_type = token_value.get("token_type")
+    expires_in = token_value.get("expires_in")
+    if (
+        token_type != "Bearer"
+        or not isinstance(access_token, str)
+        or not re.fullmatch(r"[!-~]{1,4096}", access_token)
+        or not isinstance(expires_in, int)
+        or isinstance(expires_in, bool)
+        or expires_in <= 0
+    ):
+        raise SystemExit("Runtime metadata token response was invalid.")
+
+    secret_request = urllib.request.Request(
+        RUNTIME_SECRET_ACCESS_URL,
+        headers={"Accept": "application/json", "Authorization": f"Bearer {access_token}"},
+        method="GET",
+    )
+    secret_value = _strict_json_object(
+        _read_http_response(
+            secret_request,
+            max_bytes=MAX_SECRET_RESPONSE_BYTES,
+            purpose="Scoped runtime secret access",
+        ),
+        purpose="Scoped runtime secret access",
+    )
+    payload = secret_value.get("payload")
+    encoded_secret = payload.get("data") if isinstance(payload, dict) else None
+    if not isinstance(encoded_secret, str):
+        raise SystemExit("Scoped runtime secret response was invalid.")
+    try:
+        credential_bytes = base64.b64decode(encoded_secret, validate=True)
+    except (binascii.Error, ValueError):
+        raise SystemExit("Scoped runtime secret response was invalid.") from None
+    if not credential_bytes or len(credential_bytes) > MAX_RUNTIME_SECRET_BYTES:
+        raise SystemExit("Scoped runtime secret response was invalid.")
+    if any(byte in credential_bytes for byte in (0, 10, 13)):
+        raise SystemExit("Scoped runtime secret response was invalid.")
+    try:
+        return credential_bytes.decode("utf-8", errors="strict")
+    except UnicodeDecodeError:
+        raise SystemExit("Scoped runtime secret response was invalid.") from None
+
+
 def password(args: argparse.Namespace) -> str:
    validate_runtime_connection(args)
-    if args.credential_mode == "clone-readonly" and os.environ.get("PGPASSWORD"):
+    if args.credential_mode == "runtime":
+        return runtime_password_from_metadata()
+    if os.environ.get("PGPASSWORD"):
        return os.environ["PGPASSWORD"]
-    if not args.password_secret:
-        raise SystemExit("Scoped Cloud SQL password secret is not configured.")
-    result = subprocess.run(
-        [
-            "gcloud",
-            "secrets",
-            "versions",
-            "access",
-            "latest",
-            f"--secret={args.password_secret}",
-            f"--project={args.project}",
-        ],
-        text=True,
-        capture_output=True,
-        check=False,
-    )
-    if result.returncode != 0:
-        raise SystemExit(f"Secret access failed: {result.stderr.strip()}")
-    credential = result.stdout.strip()
-    if not credential:
-        raise SystemExit("Scoped Cloud SQL password secret resolved to an empty value.")
-    return credential
+    raise SystemExit("Clone credential mode requires an inherited test credential.")


 def run_psql(args: argparse.Namespace, sql: str, db: str | None = None) -> str:
-    env = os.environ.copy()
-    for key in tuple(env):
-        if key.startswith("PG"):
-            env.pop(key, None)
+    credential = password(args)
+    if args.credential_mode == "runtime":
+        env = dict(RUNTIME_PSQL_ENV_BASE)
+    else:
+        env = {key: value for key, value in os.environ.items() if not key.startswith("PG")}
    env.update(
        {
            "PGHOST": str(args.host),
            "PGPORT": str(args.port),
            "PGDATABASE": str(db or args.db),
            "PGUSER": str(args.user),
-            "PGSSLMODE": "require",
-            "PGCONNECT_TIMEOUT": "8",
-            "PGPASSWORD": password(args),
+            "PGPASSWORD": credential,
        }
    )
    if args.credential_mode == "clone-readonly":
@ -360,9 +537,7 @@ def run_psql(args: argparse.Namespace, sql: str, db: str | None = None) -> str:
        check=False,
    )
    if result.returncode != 0:
-        raise SystemExit(
-            f"Cloud SQL query failed ({result.returncode})\nSTDOUT:\n{result.stdout}\nSTDERR:\n{result.stderr}"
-        )
+        raise SystemExit(f"Cloud SQL query failed with exit status {result.returncode}.")
    return result.stdout


@ -385,6 +560,10 @@ def database_read_marker(args: argparse.Namespace) -> dict[str, Any]:
 select jsonb_build_object(
  'database', current_database(),
  'database_user', current_user,
+  'server_addr', inet_server_addr()::text,
+  'server_port', inet_server_port(),
+  'ssl', coalesce((select ssl from pg_catalog.pg_stat_ssl where pid = pg_backend_pid()), false),
+  'ssl_version', (select version from pg_catalog.pg_stat_ssl where pid = pg_backend_pid()),
  'system_identifier', (select system_identifier::text from pg_control_system()),
  'wal_lsn', pg_current_wal_lsn()::text
 )::text;
@ -392,12 +571,34 @@ select jsonb_build_object(
    rows = psql_json_lines(args, sql, db=args.canonical_db)
    if len(rows) != 1:
        raise SystemExit("Canonical database read marker returned an invalid row count.")
-    return rows[0]
+    marker = rows[0]
+    expected_database = str(args.canonical_db or "")
+    expected_user = str(args.user or "")
+    if marker.get("database") != expected_database or marker.get("database_user") != expected_user:
+        raise SystemExit("Canonical database read marker returned an unexpected database identity.")
+    if getattr(args, "credential_mode", "runtime") == "runtime":
+        if marker.get("server_addr") != RUNTIME_CLOUDSQL_HOST:
+            raise SystemExit("Canonical database read marker returned an unexpected server address.")
+        if str(marker.get("server_port")) != RUNTIME_CLOUDSQL_PORT:
+            raise SystemExit("Canonical database read marker returned an unexpected server port.")
+        if marker.get("ssl") is not True:
+            raise SystemExit("Canonical database read marker did not prove an encrypted connection.")
+    return marker


 def _read_marker_stable(before: dict[str, Any], after: dict[str, Any]) -> bool:
    return all(
-        before.get(key) == after.get(key) for key in ("database", "database_user", "system_identifier", "wal_lsn")
+        before.get(key) == after.get(key)
+        for key in (
+            "database",
+            "database_user",
+            "server_addr",
+            "server_port",
+            "ssl",
+            "ssl_version",
+            "system_identifier",
+            "wal_lsn",
+        )
    )


@ -470,6 +671,10 @@ def build_retrieval_receipt(
            "attempts": attempts,
            "database": before.get("database"),
            "database_user": before.get("database_user"),
+            "server_addr": before.get("server_addr"),
+            "server_port": before.get("server_port"),
+            "ssl": before.get("ssl"),
+            "ssl_version": before.get("ssl_version"),
            "system_identifier": before.get("system_identifier"),
            "wal_lsn_before": before.get("wal_lsn"),
            "wal_lsn_after": after.get("wal_lsn"),
--- a/hermes-agent/leoclean-bin/teleo-kb
+++ b/hermes-agent/leoclean-bin/teleo-kb
@ -1,9 +1,15 @@
-#!/usr/bin/env bash
+#!/bin/bash
 set -euo pipefail

 PROFILE_DIR=${HERMES_HOME:-/home/teleo/.hermes/profiles/leoclean}
 KB_TOOL="$PROFILE_DIR/bin/kb_tool.py"
-CLOUDSQL_TOOL="$PROFILE_DIR/bin/cloudsql_memory_tool.py"
+SCRIPT_PATH=${BASH_SOURCE[0]}
+SCRIPT_DIR=${SCRIPT_PATH%/*}
+if [ "$SCRIPT_DIR" = "$SCRIPT_PATH" ]; then
+  SCRIPT_DIR=.
+fi
+SCRIPT_DIR="$(cd "$SCRIPT_DIR" && pwd)"
+CLOUDSQL_TOOL="$SCRIPT_DIR/cloudsql_memory_tool.py"
 MODE=${TELEO_KB_MODE:-auto}
 COMMAND=${1:-}

@ -31,17 +37,22 @@ run_cloudsql() {
    echo "teleo-kb: Cloud SQL tool is missing or not executable: $CLOUDSQL_TOOL" >&2
    exit 69
  fi
-  for dependency in python3 psql gcloud; do
-    if ! command -v "$dependency" >/dev/null 2>&1; then
-      echo "teleo-kb: required Cloud SQL dependency is unavailable: $dependency" >&2
-      exit 69
-    fi
-  done
+  if [ ! -x /usr/bin/python3 ]; then
+    echo "teleo-kb: required Cloud SQL dependency is unavailable: /usr/bin/python3" >&2
+    exit 69
+  fi
+  if ! command -v psql >/dev/null 2>&1; then
+    echo "teleo-kb: required Cloud SQL dependency is unavailable: psql" >&2
+    exit 69
+  fi
  extra_args=()
  while IFS= read -r arg; do
    [ -n "$arg" ] && extra_args+=("$arg")
  done < <(cloudsql_args)
-  exec python3 "$CLOUDSQL_TOOL" "$@" "${extra_args[@]}"
+  if [ "${#extra_args[@]}" -gt 0 ]; then
+    exec /usr/bin/python3 "$CLOUDSQL_TOOL" "$@" "${extra_args[@]}"
+  fi
+  exec /usr/bin/python3 "$CLOUDSQL_TOOL" "$@"
 }

 case "$MODE" in
@ -49,10 +60,10 @@ case "$MODE" in
    run_cloudsql "$@"
    ;;
  local)
-    exec python3 "$KB_TOOL" --local "$@"
+    exec /usr/bin/python3 "$KB_TOOL" --local "$@"
    ;;
  remote)
-    exec python3 "$KB_TOOL" "$@"
+    exec /usr/bin/python3 "$KB_TOOL" "$@"
    ;;
  auto)
    # Canonical commands must fail closed on Cloud SQL errors. Falling through
@ -62,9 +73,9 @@ case "$MODE" in
      run_cloudsql "$@"
    fi
    if command -v docker >/dev/null 2>&1; then
-      exec python3 "$KB_TOOL" --local "$@"
+      exec /usr/bin/python3 "$KB_TOOL" --local "$@"
    fi
-    exec python3 "$KB_TOOL" "$@"
+    exec /usr/bin/python3 "$KB_TOOL" "$@"
    ;;
  *)
    echo "Unsupported TELEO_KB_MODE=$MODE; expected auto, cloudsql, local, or remote" >&2
--- a/ops/gcp_leoclean_runtime_role.sql
+++ b/ops/gcp_leoclean_runtime_role.sql
@ -1,5 +1,4 @@
 \set ON_ERROR_STOP on
-\getenv runtime_password TELEO_LEOCLEAN_DB_PASSWORD

 -- One-time GCP staging provisioning for Leo's Cloud SQL identity. The password
 -- is supplied only through the process environment and is never stored here.
@ -8,7 +7,10 @@
 -- through one narrowly-scoped SECURITY DEFINER function. It cannot inherit or
 -- SET ROLE into another principal, forge the proposer identity, write directly
 -- to canonical/staging tables, or inspect the legacy teleo_restore audit schema.
-select 'create role leoclean_kb_runtime login nosuperuser nocreatedb nocreaterole noinherit noreplication nobypassrls connection limit 8'
+-- Keep the runtime unable to authenticate until both database phases have
+-- completed and verified. Any failure before the final transaction therefore
+-- leaves a disabled role instead of a partially provisioned login.
+select 'create role leoclean_kb_runtime nologin nosuperuser nocreatedb nocreaterole noinherit noreplication nobypassrls connection limit 8'
 where not exists (select 1 from pg_catalog.pg_roles where rolname = 'leoclean_kb_runtime')
 \gexec

@ -16,15 +18,19 @@ select 'create role leoclean_kb_stage_owner nologin nosuperuser nocreatedb nocre
 where not exists (select 1 from pg_catalog.pg_roles where rolname = 'leoclean_kb_stage_owner')
 \gexec

-select format('alter role leoclean_kb_runtime password %L', :'runtime_password')
-\gexec
-
 alter role leoclean_kb_runtime
-  with login nosuperuser nocreatedb nocreaterole noinherit noreplication nobypassrls connection limit 8;
+  with nologin nosuperuser nocreatedb nocreaterole noinherit noreplication nobypassrls connection limit 8;
 alter role leoclean_kb_stage_owner
  with nologin nosuperuser nocreatedb nocreaterole noinherit noreplication nobypassrls connection limit -1
  password null;

+-- Rotate the credential only after an idempotent rerun has disabled any
+-- pre-existing LOGIN role. This ordering has an intentional autocommit
+-- boundary: interruption can leave NOLOGIN, never a still-enabled old role.
+\getenv runtime_password TELEO_LEOCLEAN_DB_PASSWORD
+select format('alter role leoclean_kb_runtime password %L', :'runtime_password')
+\gexec
+
 alter role leoclean_kb_runtime reset all;
 alter role leoclean_kb_stage_owner reset all;

@ -261,7 +267,7 @@ begin
    select 1
      from pg_catalog.pg_roles role_row
     where role_row.rolname = 'leoclean_kb_runtime'
-       and (not role_row.rolcanlogin
+       and (role_row.rolcanlogin
            or role_row.rolsuper
            or role_row.rolcreatedb
            or role_row.rolcreaterole
@ -270,7 +276,7 @@ begin
            or role_row.rolbypassrls
            or role_row.rolconnlimit <> 8)
  ) then
-    raise exception 'leoclean_kb_runtime has unsafe role attributes';
+    raise exception 'leoclean_kb_runtime has unsafe provisioning role attributes';
  end if;

  if exists (
@ -818,6 +824,36 @@ commit;

 \connect teleo_canonical

+-- LOGIN is the last state change. If this verification fails, the transaction
+-- rolls back and the role remains NOLOGIN while prior least-privilege grants
+-- stay inert for direct authentication.
+begin;
+
+alter role leoclean_kb_runtime
+  with login nosuperuser nocreatedb nocreaterole noinherit noreplication nobypassrls connection limit 8;
+
+do $login_verification$
+begin
+  if exists (
+    select 1
+      from pg_catalog.pg_roles role_row
+     where role_row.rolname = 'leoclean_kb_runtime'
+       and (not role_row.rolcanlogin
+            or role_row.rolsuper
+            or role_row.rolcreatedb
+            or role_row.rolcreaterole
+            or role_row.rolinherit
+            or role_row.rolreplication
+            or role_row.rolbypassrls
+            or role_row.rolconnlimit <> 8)
+  ) then
+    raise exception 'leoclean_kb_runtime final login attributes are unsafe';
+  end if;
+end
+$login_verification$;
+
+commit;
+
 select jsonb_build_object(
  'role', rolname,
  'superuser', rolsuper,
@ -835,6 +871,7 @@ select jsonb_build_object(
  'can_select_claims', has_table_privilege(rolname, 'public.claims', 'SELECT'),
  'can_select_proposals', has_table_privilege(rolname, 'kb_stage.kb_proposals', 'SELECT'),
  'can_insert_proposals_directly', has_table_privilege(rolname, 'kb_stage.kb_proposals', 'INSERT'),
+  'can_connect_legacy_database', has_database_privilege(rolname, 'teleo_kb', 'CONNECT'),
  'can_create_database_objects', has_database_privilege(rolname, 'teleo_canonical', 'CREATE'),
  'can_create_temp_objects', has_database_privilege(rolname, 'teleo_canonical', 'TEMP'),
  'can_stage_proposal', has_function_privilege(
--- a/ops/verify_gcp_leoclean_runtime_permissions.py
+++ b/ops/verify_gcp_leoclean_runtime_permissions.py
--- a/ops/verify_gcp_leoclean_service_environment.py
+++ b/ops/verify_gcp_leoclean_service_environment.py
@ -0,0 +1,219 @@
+#!/usr/bin/env python3
+"""Verify the effective Leo service environment without exposing its values."""
+
+from __future__ import annotations
+
+import argparse
+import json
+import sys
+from collections.abc import Mapping
+from pathlib import Path
+from typing import Any
+
+PROJECT_ID = "teleo-501523"
+PRIVATE_CLOUDSQL_HOST = "10.61.0.3"
+PRIVATE_CLOUDSQL_PORT = "5432"
+CANONICAL_DATABASE = "teleo_canonical"
+RUNTIME_DATABASE_ROLE = "leoclean_kb_runtime"
+SCOPED_PASSWORD_SECRET = "gcp-teleo-pgvector-standby-leoclean-kb-runtime-password"
+ADMINISTRATOR_PASSWORD_SECRET = "gcp-teleo-pgvector-standby-postgres-password"
+RUNTIME_PATH = "/usr/local/sbin:/usr/local/bin:/usr/sbin:/usr/bin:/sbin:/bin"
+
+FORBIDDEN_EXACT_FIELDS = frozenset(
+    {
+        "ALL_PROXY",
+        "BASH_ENV",
+        "BASHOPTS",
+        "CDPATH",
+        "CURL_CA_BUNDLE",
+        "ENV",
+        "GLOBIGNORE",
+        "GOOGLE_APPLICATION_CREDENTIALS",
+        "HTTPS_PROXY",
+        "HTTP_PROXY",
+        "IFS",
+        "NO_PROXY",
+        "PS4",
+        "REQUESTS_CA_BUNDLE",
+        "SHELLOPTS",
+        "SSL_CERT_DIR",
+        "SSL_CERT_FILE",
+        "SSLKEYLOGFILE",
+    }
+)
+
+
+class VerificationError(RuntimeError):
+    """A sanitized failure safe to serialize in a public receipt."""
+
+    def __init__(self, code: str, fields: tuple[str, ...] = ()) -> None:
+        self.code = code
+        self.fields = tuple(sorted(set(fields)))
+        super().__init__(code)
+
+    def as_dict(self) -> dict[str, object]:
+        payload: dict[str, object] = {"code": self.code}
+        if self.fields:
+            payload["fields"] = list(self.fields)
+        return payload
+
+
+class _SanitizedArgumentParser(argparse.ArgumentParser):
+    def error(self, _message: str) -> None:
+        raise VerificationError("invalid_arguments")
+
+
+def validate_pid(value: str | int) -> int:
+    """Return a positive process id without retaining the input on failure."""
+
+    if isinstance(value, bool) or not isinstance(value, (str, int)):
+        raise VerificationError("invalid_pid")
+    if isinstance(value, str) and (not value.isascii() or not value.isdecimal() or value.startswith("0")):
+        raise VerificationError("invalid_pid")
+    try:
+        pid = int(value)
+    except (TypeError, ValueError):
+        raise VerificationError("invalid_pid") from None
+    if pid <= 0:
+        raise VerificationError("invalid_pid")
+    return pid
+
+
+def expected_environment() -> dict[str, str]:
+    """Build the exact reviewed environment contract."""
+
+    return {
+        "PATH": RUNTIME_PATH,
+        "TELEO_CANONICAL_CLOUDSQL_DB": CANONICAL_DATABASE,
+        "TELEO_CLOUDSQL_DB": CANONICAL_DATABASE,
+        "TELEO_CLOUDSQL_ENABLE_AUDIT_FALLBACK": "0",
+        "TELEO_CLOUDSQL_HOST": PRIVATE_CLOUDSQL_HOST,
+        "TELEO_CLOUDSQL_PASSWORD_SECRET": SCOPED_PASSWORD_SECRET,
+        "TELEO_CLOUDSQL_PORT": PRIVATE_CLOUDSQL_PORT,
+        "TELEO_CLOUDSQL_USER": RUNTIME_DATABASE_ROLE,
+        "TELEO_GCP_METADATA_ONLY": "1",
+        "TELEO_GCP_PROJECT": PROJECT_ID,
+        "TELEO_KB_MODE": "cloudsql",
+    }
+
+
+def parse_environment(raw: bytes) -> dict[str, str]:
+    """Parse a Linux ``/proc/PID/environ`` block and reject ambiguity."""
+
+    if not isinstance(raw, bytes) or not raw or not raw.endswith(b"\0"):
+        raise VerificationError("environment_malformed")
+
+    records = raw[:-1].split(b"\0")
+    if any(not record for record in records):
+        raise VerificationError("environment_malformed")
+
+    environment: dict[str, str] = {}
+    try:
+        for record in records:
+            encoded_key, separator, encoded_value = record.partition(b"=")
+            if not separator or not encoded_key:
+                raise VerificationError("environment_malformed")
+            key = encoded_key.decode("utf-8", "strict")
+            value = encoded_value.decode("utf-8", "strict")
+            if key in environment:
+                raise VerificationError("environment_malformed")
+            environment[key] = value
+    except UnicodeDecodeError:
+        raise VerificationError("environment_malformed") from None
+    return environment
+
+
+def _forbidden_field_labels(environment: Mapping[str, str]) -> tuple[str, ...]:
+    labels: set[str] = set()
+    for key in environment:
+        normalized = key.upper()
+        if normalized.startswith("PG"):
+            labels.add("PG*")
+        if normalized.startswith("CLOUDSDK_"):
+            labels.add("CLOUDSDK_*")
+        if normalized.startswith("LD_"):
+            labels.add("LD_*")
+        if normalized.startswith("BASH_FUNC_"):
+            labels.add("BASH_FUNC_*")
+        if normalized.startswith("PYTHON") and normalized != "PYTHONUNBUFFERED":
+            labels.add("PYTHON*")
+        if normalized in FORBIDDEN_EXACT_FIELDS:
+            labels.add(normalized)
+    return tuple(sorted(labels))
+
+
+def validate_environment(environment: Mapping[str, str]) -> tuple[str, ...]:
+    """Validate the effective environment and return only reviewed field names."""
+
+    if not isinstance(environment, Mapping) or any(
+        not isinstance(key, str) or not isinstance(value, str) for key, value in environment.items()
+    ):
+        raise VerificationError("environment_malformed")
+
+    expected = expected_environment()
+    administrator_secret = ADMINISTRATOR_PASSWORD_SECRET.casefold()
+    if any(administrator_secret in value.casefold() for value in environment.values()):
+        raise VerificationError("administrator_secret_reference")
+
+    forbidden_fields = _forbidden_field_labels(environment)
+    if forbidden_fields:
+        raise VerificationError("forbidden_environment_fields", forbidden_fields)
+
+    mismatched = tuple(
+        sorted(key for key, expected_value in expected.items() if environment.get(key) != expected_value)
+    )
+    if mismatched:
+        raise VerificationError("environment_mismatch", mismatched)
+
+    return tuple(sorted(expected))
+
+
+def verify_process_environment(
+    pid: int,
+    *,
+    proc_root: Path = Path("/proc"),
+) -> dict[str, object]:
+    """Read and verify one process environment, returning a sanitized receipt."""
+
+    validated_pid = validate_pid(pid)
+    raw = (proc_root / str(validated_pid) / "environ").read_bytes()
+    validated_fields = validate_environment(parse_environment(raw))
+    return {
+        "runtime_environment": "scoped",
+        "status": "pass",
+        "validated_fields": list(validated_fields),
+    }
+
+
+def failure_receipt(error: VerificationError) -> dict[str, object]:
+    return {"error": error.as_dict(), "status": "fail"}
+
+
+def canonical_json(payload: Mapping[str, Any]) -> str:
+    return json.dumps(payload, ensure_ascii=True, separators=(",", ":"), sort_keys=True) + "\n"
+
+
+def parse_args(argv: list[str] | None = None) -> argparse.Namespace:
+    parser = _SanitizedArgumentParser(description=__doc__, add_help=False)
+    parser.add_argument("--pid", required=True)
+    return parser.parse_args(argv)
+
+
+def main(argv: list[str] | None = None) -> int:
+    try:
+        args = parse_args(argv)
+        receipt = verify_process_environment(validate_pid(args.pid))
+        returncode = 0
+    except VerificationError as exc:
+        receipt = failure_receipt(exc)
+        returncode = 1
+    except Exception:
+        receipt = failure_receipt(VerificationError("internal_error"))
+        returncode = 1
+
+    sys.stdout.write(canonical_json(receipt))
+    return returncode
+
+
+if __name__ == "__main__":
+    raise SystemExit(main())
--- a/scripts/run_gcp_generated_db_direct_claim_suite.py
+++ b/scripts/run_gcp_generated_db_direct_claim_suite.py
@ -47,7 +47,7 @@ DEFAULT_HOST = "10.61.0.3"
 DEFAULT_PROJECT = "teleo-501523"
 DEFAULT_SECRET = "gcp-teleo-pgvector-standby-postgres-password"
 DEFAULT_MANIFEST_SQL = HERE.parent / "ops" / "postgres_parity_manifest.sql"
-REVIEWED_CLOUDSQL_TOOL_SHA256 = "2617bb501456758131ff41a6c77b3c462e21c28c4348da319b60defb051c7c87"
+REVIEWED_CLOUDSQL_TOOL_SHA256 = "66fa84b3bd6fe67e102fbce4509ea28c3537ba5bb1091e1a1a457b7425366064"
 REVIEWED_MANIFEST_SQL_SHA256 = "8b8cdc25d54fdd8de05eb38c6e4423d2836953eb6012d4545f5c9c71b5f0150a"
 COUNT_READBACK_RE = re.compile(
    r"DB readback:\s*claims:\s*`?(?P<claims>\d+)`?;\s*"
--- a/systemd/leoclean-gcp-prod-parallel-cloudsql.conf
+++ b/systemd/leoclean-gcp-prod-parallel-cloudsql.conf
@ -1,9 +1,19 @@
 [Service]
 UnsetEnvironment=PGPASSWORD
-RuntimeDirectory=leoclean-gcp-prod-parallel
-RuntimeDirectoryMode=0700
-Environment=CLOUDSDK_CONFIG=/run/leoclean-gcp-prod-parallel
+UnsetEnvironment=PGPASSFILE PGSERVICE PGHOST PGPORT PGDATABASE PGUSER PGOPTIONS
+UnsetEnvironment=GOOGLE_APPLICATION_CREDENTIALS CLOUDSDK_CONFIG CLOUDSDK_CORE_PROJECT CLOUDSDK_AUTH_ACCESS_TOKEN
+UnsetEnvironment=BASH_ENV ENV BASHOPTS SHELLOPTS CDPATH GLOBIGNORE IFS PS4
+UnsetEnvironment=LD_PRELOAD LD_LIBRARY_PATH LD_AUDIT LD_DEBUG LD_DEBUG_OUTPUT LD_DYNAMIC_WEAK LD_HWCAP_MASK LD_ORIGIN_PATH LD_PROFILE LD_SHOW_AUXV LD_TRACE_LOADED_OBJECTS LD_USE_LOAD_BIAS LD_VERBOSE LD_WARN
+UnsetEnvironment=PYTHONHOME PYTHONPATH PYTHONSTARTUP PYTHONINSPECT PYTHONUSERBASE PYTHONHTTPSVERIFY
+UnsetEnvironment=HTTP_PROXY HTTPS_PROXY ALL_PROXY NO_PROXY http_proxy https_proxy all_proxy no_proxy
+UnsetEnvironment=SSL_CERT_FILE SSL_CERT_DIR REQUESTS_CA_BUNDLE CURL_CA_BUNDLE SSLKEYLOGFILE
+ReadOnlyPaths=/home/teleo/.hermes
+ReadWritePaths=/home/teleo/.hermes/profiles/leoclean/state /home/teleo/.hermes/profiles/leoclean/workspace
+BindReadOnlyPaths=/usr/local/libexec/livingip/leoclean-kb:/home/teleo/.hermes/profiles/leoclean/bin
+CapabilityBoundingSet=~CAP_SYS_ADMIN
+Environment=PATH=/usr/local/sbin:/usr/local/bin:/usr/sbin:/usr/bin:/sbin:/bin
 Environment=TELEO_KB_MODE=cloudsql
+Environment=TELEO_GCP_METADATA_ONLY=1
 Environment=TELEO_GCP_PROJECT=teleo-501523
 Environment=TELEO_CLOUDSQL_HOST=10.61.0.3
 Environment=TELEO_CLOUDSQL_PORT=5432
--- a/tests/test_gcp_leoclean_runtime_permissions.py
+++ b/tests/test_gcp_leoclean_runtime_permissions.py
@ -0,0 +1,797 @@
+import hashlib
+import json
+import os
+import stat
+import subprocess
+from collections.abc import Mapping
+from pathlib import Path
+
+import pytest
+
+from ops import verify_gcp_leoclean_runtime_permissions as verifier
+
+RUN_ID = "20260715-leo-security"
+SOURCE_REF = f"leo-runtime-permission:{RUN_ID}"
+SECRET_VALUE = "unit-only-secret-value%42"
+AGENT_ID = "11111111-1111-4111-8111-111111111111"
+
+
+class FakeRunner:
+    def __init__(
+        self,
+        *,
+        sqlstate_override: tuple[str, str] | None = None,
+        sqlstate_missing_for: str | None = None,
+        unexpected_success_for: str | None = None,
+        scoped_failure: bool = False,
+        administrator_mode: str = "denied",
+        identity_override: Mapping[str, object] | None = None,
+        role_posture_override: Mapping[str, object] | None = None,
+        stage_owner_role_posture_override: Mapping[str, object] | None = None,
+        function_posture_override: Mapping[str, Mapping[str, object]] | None = None,
+        stage_definition_override: Mapping[str, object] | None = None,
+        catalog_posture_override: Mapping[str, object] | None = None,
+        legacy_catalog_posture_override: Mapping[str, object] | None = None,
+    ) -> None:
+        self.sqlstate_override = sqlstate_override
+        self.sqlstate_missing_for = sqlstate_missing_for
+        self.unexpected_success_for = unexpected_success_for
+        self.scoped_failure = scoped_failure
+        self.administrator_mode = administrator_mode
+        self.identity_override = dict(identity_override or {})
+        self.role_posture_override = dict(role_posture_override or {})
+        self.stage_owner_role_posture_override = dict(stage_owner_role_posture_override or {})
+        self.function_posture_override = {
+            name: dict(values) for name, values in (function_posture_override or {}).items()
+        }
+        self.stage_definition_override = dict(stage_definition_override or {})
+        self.catalog_posture_override = dict(catalog_posture_override or {})
+        self.legacy_catalog_posture_override = dict(legacy_catalog_posture_override or {})
+        self.calls: list[tuple[list[str], dict[str, str], int, bool]] = []
+        self.negative = {check.sql: check for check in verifier._negative_checks(RUN_ID, SOURCE_REF)}
+
+    def __call__(
+        self,
+        command: list[str],
+        env: Mapping[str, str],
+        timeout: int,
+        discard_stdout: bool,
+    ) -> verifier.CommandResult:
+        self.calls.append((list(command), dict(env), timeout, discard_stdout))
+
+        if command[0] == verifier.GCLOUD_BIN:
+            scoped = f"--secret={verifier.SCOPED_PASSWORD_SECRET}" in command
+            if scoped:
+                if self.scoped_failure:
+                    return verifier.CommandResult(1, SECRET_VALUE, f"scoped failure {SECRET_VALUE}")
+                return verifier.CommandResult(0, f"{SECRET_VALUE}\n", f"ignored warning {SECRET_VALUE}")
+            assert f"--secret={verifier.ADMINISTRATOR_PASSWORD_SECRET}" in command
+            assert discard_stdout is True
+            if self.administrator_mode == "success":
+                return verifier.CommandResult(0, SECRET_VALUE, f"ignored {SECRET_VALUE}")
+            if self.administrator_mode == "wrong-error":
+                return verifier.CommandResult(1, SECRET_VALUE, f"network unavailable {SECRET_VALUE}")
+            return verifier.CommandResult(
+                1,
+                SECRET_VALUE,
+                (
+                    "ERROR: PERMISSION_DENIED: Permission "
+                    f"'{verifier.IAM_PERMISSION}' denied for the administrator secret; {SECRET_VALUE}"
+                ),
+            )
+
+        assert command[0] == verifier.PSQL_BIN
+        assert discard_stdout is False
+        sql = next(part.removeprefix("--command=") for part in command if part.startswith("--command="))
+
+        if sql == verifier._identity_sql():
+            identity: dict[str, object] = {
+                "current_user": verifier.RUNTIME_DATABASE_ROLE,
+                "database": verifier.CANONICAL_DATABASE,
+                "leak": SECRET_VALUE,
+                "server_addr": verifier.PRIVATE_CLOUDSQL_HOST,
+                "server_port": verifier.PRIVATE_CLOUDSQL_PORT,
+                "session_user": verifier.RUNTIME_DATABASE_ROLE,
+                "ssl": True,
+                "ssl_version": "TLSv1.3",
+            }
+            identity.update(self.identity_override)
+            return verifier.CommandResult(0, json.dumps(identity), f"ignored {SECRET_VALUE}")
+        if sql == verifier._allowed_read_sql():
+            return verifier.CommandResult(
+                0,
+                json.dumps(
+                    {
+                        "claims_rows_sampled": 1,
+                        "leak": SECRET_VALUE,
+                        "proposal_rows_sampled": 0,
+                    }
+                ),
+                f"ignored {SECRET_VALUE}",
+            )
+        if sql == verifier._role_posture_sql():
+            role_posture: dict[str, object] = {
+                "bypasses_rls": False,
+                "can_create_db": False,
+                "can_create_role": False,
+                "can_login": True,
+                "can_replicate": False,
+                "connection_limit": 8,
+                "direct_membership_edges": 0,
+                "inherits_privileges": False,
+                "is_superuser": False,
+                "leak": SECRET_VALUE,
+                "role": verifier.RUNTIME_DATABASE_ROLE,
+            }
+            role_posture.update(self.role_posture_override)
+            return verifier.CommandResult(0, json.dumps(role_posture), f"ignored {SECRET_VALUE}")
+        if sql == verifier._stage_owner_role_posture_sql():
+            owner_posture: dict[str, object] = {
+                "bypasses_rls": False,
+                "can_create_db": False,
+                "can_create_role": False,
+                "can_login": False,
+                "can_replicate": False,
+                "connection_limit": -1,
+                "direct_membership_edges": 0,
+                "inherits_privileges": False,
+                "is_superuser": False,
+                "leak": SECRET_VALUE,
+                "role": verifier.STAGE_OWNER_DATABASE_ROLE,
+            }
+            owner_posture.update(self.stage_owner_role_posture_override)
+            return verifier.CommandResult(0, json.dumps(owner_posture), f"ignored {SECRET_VALUE}")
+        if sql == verifier._function_privilege_posture_sql():
+            function_posture: dict[str, dict[str, object]] = {
+                name: {
+                    "execute": expected_execute,
+                    "exists": expected_exists,
+                    "leak": SECRET_VALUE,
+                }
+                for name, _signature, expected_exists, expected_execute in verifier.FUNCTION_PRIVILEGE_EXPECTATIONS
+            }
+            for name, override in self.function_posture_override.items():
+                function_posture.setdefault(name, {}).update(override)
+            function_posture["unexpected_leak"] = {"value": SECRET_VALUE}
+            return verifier.CommandResult(0, json.dumps(function_posture), f"ignored {SECRET_VALUE}")
+        if sql == verifier._stage_function_definition_sql():
+            stage_definition: dict[str, object] = {
+                "acl_exact": True,
+                "argument_modes": None,
+                "configuration": ["search_path=pg_catalog, pg_temp"],
+                "exists": True,
+                "leak": SECRET_VALUE,
+                "runtime_execute": True,
+                "source": verifier.EXPECTED_STAGE_FUNCTION_SOURCE,
+                **dict(verifier.STAGE_FUNCTION_METADATA_EXPECTATIONS),
+            }
+            stage_definition.update(self.stage_definition_override)
+            return verifier.CommandResult(0, json.dumps(stage_definition), f"ignored {SECRET_VALUE}")
+        if sql == verifier._catalog_privilege_posture_sql():
+            catalog_posture: dict[str, object] = {
+                field: 0 for field in verifier.CATALOG_ZERO_COUNT_FIELDS
+            }
+            catalog_posture.update(
+                {
+                    "leak": SECRET_VALUE,
+                    **{field: True for field in verifier.CATALOG_TRUE_FIELDS},
+                }
+            )
+            catalog_posture.update(self.catalog_posture_override)
+            return verifier.CommandResult(0, json.dumps(catalog_posture), f"ignored {SECRET_VALUE}")
+        if sql == verifier._legacy_catalog_privilege_posture_sql():
+            legacy_posture: dict[str, object] = {
+                field: 0 for field in verifier.LEGACY_CATALOG_ZERO_COUNT_FIELDS
+            }
+            legacy_posture["leak"] = SECRET_VALUE
+            legacy_posture.update(self.legacy_catalog_posture_override)
+            return verifier.CommandResult(0, json.dumps(legacy_posture), f"ignored {SECRET_VALUE}")
+        if sql == verifier._canary_count_sql(SOURCE_REF):
+            return verifier.CommandResult(0, "0\n", f"ignored {SECRET_VALUE}")
+        if sql == verifier._stage_sql(RUN_ID, SOURCE_REF):
+            return verifier.CommandResult(
+                0,
+                json.dumps(
+                    {
+                        "agent_id_matches": True,
+                        "proposal": {
+                            "leak": SECRET_VALUE,
+                            "proposed_by_agent_id": AGENT_ID,
+                            "proposed_by_handle": "leo",
+                            "source_ref": SOURCE_REF,
+                            "status": "pending_review",
+                        },
+                    }
+                ),
+                f"ignored {SECRET_VALUE}",
+            )
+
+        check = self.negative[sql]
+        if check.name == self.unexpected_success_for:
+            return verifier.CommandResult(0, SECRET_VALUE, f"unexpected success {SECRET_VALUE}")
+        if check.name == self.sqlstate_missing_for:
+            return verifier.CommandResult(1, SECRET_VALUE, f"denied without state {SECRET_VALUE}")
+        observed = check.expected_sqlstate
+        if self.sqlstate_override is not None and check.name == self.sqlstate_override[0]:
+            observed = self.sqlstate_override[1]
+        return verifier.CommandResult(
+            1,
+            SECRET_VALUE,
+            f"ERROR:  {observed}: expected test denial; {SECRET_VALUE}\nLOCATION: test",
+        )
+
+
+def poisoned_environment() -> dict[str, str]:
+    return {
+        "CLOUDSDK_AUTH_ACCESS_TOKEN": "must-not-reach-gcloud",
+        "GOOGLE_APPLICATION_CREDENTIALS": "/tmp/must-not-reach-gcloud.json",
+        "HOME": "/home/teleo",
+        "LANG": "C.UTF-8",
+        "LD_PRELOAD": "/tmp/must-not-load.so",
+        "OTHER": "preserved",
+        "PGDATABASE": "wrong-db",
+        "PGHOST": "public.example.invalid",
+        "PGPASSWORD": "administrator-password",
+        "PGSERVICE": "broad-service",
+        "pgsslmode": "disable",
+    }
+
+
+def run_success(runner: FakeRunner) -> dict[str, object]:
+    return verifier.verify_runtime_permissions(
+        RUN_ID,
+        runner=runner,
+        base_env=poisoned_environment(),
+        effective_user="teleo",
+    )
+
+
+def assert_child_boundaries(runner: FakeRunner) -> None:
+    assert runner.calls
+    for command, env, timeout, discard_stdout in runner.calls:
+        assert SECRET_VALUE not in "\n".join(command)
+        assert timeout == verifier.COMMAND_TIMEOUT_SECONDS
+        pg_keys = sorted(key for key in env if key.upper().startswith("PG"))
+        if command[0] == verifier.PSQL_BIN:
+            assert pg_keys == ["PGPASSWORD"]
+            assert env["PGPASSWORD"] == SECRET_VALUE
+            assert discard_stdout is False
+        else:
+            assert pg_keys == []
+            assert "CLOUDSDK_AUTH_ACCESS_TOKEN" not in env
+            assert "GOOGLE_APPLICATION_CREDENTIALS" not in env
+        assert env["HOME"] == "/home/teleo"
+        assert env["LANG"] == "C"
+        assert env["LC_ALL"] == "C"
+        assert env["PATH"] == verifier.CHILD_PATH
+        assert "LD_PRELOAD" not in env
+        assert "OTHER" not in env
+
+
+def test_live_receipt_contract_is_sanitized_and_uses_exact_child_environments() -> None:
+    runner = FakeRunner()
+
+    receipt = run_success(runner)
+    serialized = verifier.canonical_json(receipt)
+
+    assert receipt["status"] == "pass"
+    assert receipt["current_tier"] == verifier.REQUIRED_TIER
+    assert receipt["database_identity"] == {
+        "current_user": verifier.RUNTIME_DATABASE_ROLE,
+        "database": verifier.CANONICAL_DATABASE,
+        "server_addr": verifier.PRIVATE_CLOUDSQL_HOST,
+        "server_port": verifier.PRIVATE_CLOUDSQL_PORT,
+        "session_user": verifier.RUNTIME_DATABASE_ROLE,
+        "ssl": True,
+        "ssl_version": "TLSv1.3",
+    }
+    assert receipt["checks"]["rolled_back_proposal"] == {
+        "agent_id_matches": True,
+        "proposed_by_agent_id": AGENT_ID,
+        "proposed_by_handle": "leo",
+        "source_ref": SOURCE_REF,
+        "status": "pending_review",
+        "transaction": "rolled_back",
+    }
+    assert receipt["checks"]["canary_rows_before"] == 0
+    assert receipt["checks"]["canary_rows_after"] == 0
+    assert receipt["checks"]["role_posture"] == {
+        "bypasses_rls": False,
+        "can_create_db": False,
+        "can_create_role": False,
+        "can_login": True,
+        "can_replicate": False,
+        "connection_limit": 8,
+        "direct_membership_edges": 0,
+        "inherits_privileges": False,
+        "is_superuser": False,
+        "role": verifier.RUNTIME_DATABASE_ROLE,
+    }
+    assert receipt["checks"]["stage_owner_role_posture"] == {
+        "bypasses_rls": False,
+        "can_create_db": False,
+        "can_create_role": False,
+        "can_login": False,
+        "can_replicate": False,
+        "connection_limit": -1,
+        "direct_membership_edges": 0,
+        "inherits_privileges": False,
+        "is_superuser": False,
+        "role": verifier.STAGE_OWNER_DATABASE_ROLE,
+    }
+    assert receipt["checks"]["function_privileges"] == {
+        name: {
+            "execute": expected_execute,
+            "exists": expected_exists,
+            "signature": signature,
+        }
+        for name, signature, expected_exists, expected_execute in verifier.FUNCTION_PRIVILEGE_EXPECTATIONS
+    }
+    assert receipt["checks"]["catalog_privileges"] == {
+        **{field: 0 for field in verifier.CATALOG_ZERO_COUNT_FIELDS},
+        **{field: True for field in verifier.CATALOG_TRUE_FIELDS},
+    }
+    assert receipt["checks"]["legacy_catalog_privileges"] == {
+        field: 0 for field in verifier.LEGACY_CATALOG_ZERO_COUNT_FIELDS
+    }
+    assert receipt["checks"]["stage_function_definition"] == {
+        "acl_exact": True,
+        "argument_modes": None,
+        "configuration": ["search_path=pg_catalog, pg_temp"],
+        "exists": True,
+        **dict(verifier.STAGE_FUNCTION_METADATA_EXPECTATIONS),
+        "runtime_execute": True,
+        "signature": verifier.STAGE_FUNCTION_SIGNATURE,
+        "source_sha256": verifier.EXPECTED_STAGE_FUNCTION_SOURCE_SHA256,
+    }
+    assert len(receipt["checks"]["negative_permissions"]) == len(verifier._negative_checks(RUN_ID, SOURCE_REF))
+    assert receipt["secret_access"]["administrator"]["classification"] == "iam_permission_denied"
+    assert receipt["secret_access"]["administrator"]["stdout_discarded"] is True
+    assert SECRET_VALUE not in serialized
+    assert "administrator-password" not in serialized
+    assert "stage_leoclean_proposal is restricted" not in serialized
+    assert_child_boundaries(runner)
+
+    administrator_call = runner.calls[-1]
+    assert administrator_call[0][0] == verifier.GCLOUD_BIN
+    assert administrator_call[3] is True
+
+
+@pytest.mark.parametrize(
+    ("attribute", "unsafe_value"),
+    [
+        ("can_login", False),
+        ("is_superuser", True),
+        ("can_create_db", True),
+        ("can_create_role", True),
+        ("inherits_privileges", True),
+        ("can_replicate", True),
+        ("bypasses_rls", True),
+        ("connection_limit", 7),
+    ],
+)
+def test_any_unsafe_runtime_role_attribute_fails_closed(attribute: str, unsafe_value: object) -> None:
+    runner = FakeRunner(role_posture_override={attribute: unsafe_value})
+
+    with pytest.raises(verifier.VerificationError) as caught:
+        run_success(runner)
+
+    assert caught.value.code == "runtime_role_posture_mismatch"
+    assert caught.value.check == "runtime_role_posture"
+    assert SECRET_VALUE not in str(caught.value)
+
+
+def test_any_direct_runtime_role_membership_edge_fails_closed() -> None:
+    runner = FakeRunner(role_posture_override={"direct_membership_edges": 1})
+
+    with pytest.raises(verifier.VerificationError) as caught:
+        run_success(runner)
+
+    assert caught.value.code == "runtime_role_posture_mismatch"
+    assert caught.value.check == "runtime_role_posture"
+
+
+@pytest.mark.parametrize(
+    ("attribute", "unsafe_value"),
+    [
+        ("role", "unexpected-owner"),
+        ("can_login", True),
+        ("is_superuser", True),
+        ("can_create_db", True),
+        ("can_create_role", True),
+        ("inherits_privileges", True),
+        ("can_replicate", True),
+        ("bypasses_rls", True),
+        ("connection_limit", 0),
+        ("direct_membership_edges", 1),
+    ],
+)
+def test_any_unsafe_stage_owner_role_posture_fails_closed(attribute: str, unsafe_value: object) -> None:
+    runner = FakeRunner(stage_owner_role_posture_override={attribute: unsafe_value})
+
+    with pytest.raises(verifier.VerificationError) as caught:
+        run_success(runner)
+
+    assert caught.value.code == "stage_owner_role_posture_mismatch"
+    assert caught.value.check == "stage_owner_role_posture"
+    assert SECRET_VALUE not in str(caught.value)
+
+
+@pytest.mark.parametrize(
+    "function_name",
+    ["approve_strict_proposal", "assert_approved_proposal", "finish_approved_proposal"],
+)
+def test_reviewer_or_apply_execute_grant_fails_closed(function_name: str) -> None:
+    runner = FakeRunner(function_posture_override={function_name: {"execute": True}})
+
+    with pytest.raises(verifier.VerificationError) as caught:
+        run_success(runner)
+
+    assert caught.value.code == "function_privilege_posture_mismatch"
+    assert caught.value.check == "function_privilege_posture"
+
+
+@pytest.mark.parametrize(
+    "function_name",
+    [
+        "stage_leoclean_proposal_5_arg",
+        "approve_strict_proposal",
+        "assert_approved_proposal",
+        "finish_approved_proposal",
+    ],
+)
+def test_missing_expected_exact_function_fails_closed(function_name: str) -> None:
+    runner = FakeRunner(function_posture_override={function_name: {"execute": False, "exists": False}})
+
+    with pytest.raises(verifier.VerificationError) as caught:
+        run_success(runner)
+
+    assert caught.value.code == "function_privilege_posture_mismatch"
+    assert caught.value.check == "function_privilege_posture"
+
+
+def test_forged_overload_presence_or_missing_stage_execute_fails_closed() -> None:
+    forged = FakeRunner(function_posture_override={"stage_leoclean_proposal_6_arg": {"exists": True}})
+    missing_execute = FakeRunner(function_posture_override={"stage_leoclean_proposal_5_arg": {"execute": False}})
+
+    for runner in (forged, missing_execute):
+        with pytest.raises(verifier.VerificationError) as caught:
+            run_success(runner)
+        assert caught.value.code == "function_privilege_posture_mismatch"
+
+
+def _drifted_value(expected: object) -> object:
+    if isinstance(expected, bool):
+        return not expected
+    if isinstance(expected, int):
+        return expected + 1
+    if isinstance(expected, str):
+        return f"{expected}-drift"
+    if isinstance(expected, list):
+        return [*expected, "drift"]
+    raise AssertionError(f"unsupported test expectation type: {type(expected).__name__}")
+
+
+@pytest.mark.parametrize(
+    ("field", "unsafe_value"),
+    [
+        (field, _drifted_value(expected))
+        for field, expected in verifier.STAGE_FUNCTION_METADATA_EXPECTATIONS
+    ],
+)
+def test_any_stage_function_metadata_drift_fails_closed(field: str, unsafe_value: object) -> None:
+    runner = FakeRunner(stage_definition_override={field: unsafe_value})
+
+    with pytest.raises(verifier.VerificationError) as caught:
+        run_success(runner)
+
+    assert caught.value.code == "stage_function_definition_mismatch"
+    assert caught.value.check == "stage_function_definition"
+    assert SECRET_VALUE not in str(caught.value)
+
+
+@pytest.mark.parametrize(
+    ("field", "unsafe_value"),
+    [
+        ("exists", False),
+        ("argument_modes", ["i", "i", "i", "i", "i"]),
+        ("configuration", ["search_path=public"]),
+        ("acl_exact", False),
+        ("runtime_execute", False),
+        ("leakproof", 0),
+        ("argument_defaults", False),
+    ],
+)
+def test_any_stage_function_contract_drift_fails_closed(field: str, unsafe_value: object) -> None:
+    runner = FakeRunner(stage_definition_override={field: unsafe_value})
+
+    with pytest.raises(verifier.VerificationError) as caught:
+        run_success(runner)
+
+    assert caught.value.code == "stage_function_definition_mismatch"
+    assert caught.value.check == "stage_function_definition"
+
+
+@pytest.mark.parametrize(
+    "unsafe_source",
+    [
+        None,
+        42,
+        verifier.EXPECTED_STAGE_FUNCTION_SOURCE.replace("return to_jsonb(staged);", "return '{}'::jsonb;"),
+        "x" * (verifier.MAX_STAGE_FUNCTION_SOURCE_BYTES + 1),
+    ],
+)
+def test_missing_malformed_oversized_or_semantically_drifted_stage_body_fails_closed(
+    unsafe_source: object,
+) -> None:
+    runner = FakeRunner(stage_definition_override={"source": unsafe_source})
+
+    with pytest.raises(verifier.VerificationError) as caught:
+        run_success(runner)
+
+    assert caught.value.code == "stage_function_definition_mismatch"
+    assert caught.value.check == "stage_function_definition"
+    failure = verifier.canonical_json(verifier.failure_receipt(RUN_ID, caught.value))
+    assert "stage_leoclean_proposal is restricted" not in failure
+    assert SECRET_VALUE not in failure
+
+
+def test_stage_body_normalization_accepts_only_line_ending_and_framing_newline_changes() -> None:
+    crlf_source = "\r\n" + verifier.EXPECTED_STAGE_FUNCTION_SOURCE.strip("\n").replace("\n", "\r\n") + "\r\n"
+
+    receipt = run_success(FakeRunner(stage_definition_override={"source": crlf_source}))
+
+    assert (
+        receipt["checks"]["stage_function_definition"]["source_sha256"]
+        == verifier.EXPECTED_STAGE_FUNCTION_SOURCE_SHA256
+    )
+
+
+def test_embedded_stage_body_attestation_is_tied_to_the_provisioning_sql_source() -> None:
+    provisioning_sql = (
+        Path(__file__).resolve().parents[1] / "ops" / "gcp_leoclean_runtime_role.sql"
+    ).read_text(encoding="utf-8")
+    function_anchor = "create or replace function kb_stage.stage_leoclean_proposal("
+    assert provisioning_sql.count(function_anchor) == 1
+    function_section = provisioning_sql.split(function_anchor, 1)[1]
+    assert function_section.count("as $function$") == 1
+    provisioned_source = function_section.split("as $function$", 1)[1].split("$function$;", 1)[0]
+
+    assert provisioned_source == verifier.EXPECTED_STAGE_FUNCTION_SOURCE
+    assert (
+        hashlib.sha256(verifier.normalize_stage_function_source(provisioned_source).encode("utf-8")).hexdigest()
+        == verifier.EXPECTED_STAGE_FUNCTION_SOURCE_SHA256
+    )
+
+
+def test_catalog_queries_use_exact_regprocedure_signatures_and_both_membership_directions() -> None:
+    function_sql = verifier._function_privilege_posture_sql()
+    role_sql = verifier._role_posture_sql()
+    owner_role_sql = verifier._stage_owner_role_posture_sql()
+    stage_definition_sql = verifier._stage_function_definition_sql()
+    catalog_sql = verifier._catalog_privilege_posture_sql()
+    legacy_sql = verifier._legacy_catalog_privilege_posture_sql()
+
+    assert "pg_catalog.to_regprocedure(signature)" in function_sql
+    for _name, signature, _exists, _execute in verifier.FUNCTION_PRIVILEGE_EXPECTATIONS:
+        assert signature in function_sql
+    assert "membership.roleid = role_row.oid" in role_sql
+    assert "membership.member = role_row.oid" in role_sql
+    assert "membership.roleid = role_row.oid" in owner_role_sql
+    assert "membership.member = role_row.oid" in owner_role_sql
+    assert verifier.STAGE_OWNER_DATABASE_ROLE in owner_role_sql
+    assert verifier.STAGE_FUNCTION_SIGNATURE in stage_definition_sql
+    assert "left join pg_catalog.pg_proc" in stage_definition_sql
+    assert "function_catalog.prosrc" in stage_definition_sql
+    assert "function_catalog.prokind" in stage_definition_sql
+    assert "function_catalog.proargtypes" in stage_definition_sql
+    assert "function_catalog.prosecdef" in stage_definition_sql
+    assert "pg_catalog.pg_get_function_result" in stage_definition_sql
+    assert "pg_catalog.aclexplode" in stage_definition_sql
+    assert "pg_catalog.pg_shdepend" in catalog_sql
+    assert "pg_catalog.has_table_privilege" in catalog_sql
+    assert "pg_catalog.has_column_privilege" in catalog_sql
+    assert "pg_catalog.has_sequence_privilege" in catalog_sql
+    assert "pg_catalog.has_function_privilege" in catalog_sql
+    assert "pg_catalog.aclexplode" in catalog_sql
+    assert "nspname !~ '^pg_'" in catalog_sql
+    assert "nspname <> 'information_schema'" in catalog_sql
+    assert verifier.STAGE_OWNER_DATABASE_ROLE in catalog_sql
+    assert "teleo_restore" in legacy_sql
+    assert "pg_catalog.has_schema_privilege" in legacy_sql
+    assert "pg_catalog.has_table_privilege" in legacy_sql
+    assert "pg_catalog.has_column_privilege" in legacy_sql
+    assert "pg_catalog.has_sequence_privilege" in legacy_sql
+    assert "pg_catalog.has_function_privilege" in legacy_sql
+    for schema, relation in verifier.READ_TABLE_ALLOWLIST:
+        assert schema in catalog_sql
+        assert relation in catalog_sql
+
+
+@pytest.mark.parametrize("field", verifier.CATALOG_ZERO_COUNT_FIELDS)
+def test_any_unexpected_catalog_privilege_fails_closed(field: str) -> None:
+    runner = FakeRunner(catalog_posture_override={field: 1})
+
+    with pytest.raises(verifier.VerificationError) as caught:
+        run_success(runner)
+
+    assert caught.value.code == "catalog_privilege_posture_mismatch"
+    assert caught.value.check == "catalog_privilege_posture"
+    assert SECRET_VALUE not in str(caught.value)
+
+
+@pytest.mark.parametrize("field", verifier.CATALOG_TRUE_FIELDS)
+def test_any_missing_required_catalog_privilege_fails_closed(field: str) -> None:
+    runner = FakeRunner(catalog_posture_override={field: False})
+
+    with pytest.raises(verifier.VerificationError) as caught:
+        run_success(runner)
+
+    assert caught.value.code == "catalog_privilege_posture_mismatch"
+
+
+@pytest.mark.parametrize("field", verifier.LEGACY_CATALOG_ZERO_COUNT_FIELDS)
+def test_any_teleo_restore_catalog_privilege_fails_closed(field: str) -> None:
+    runner = FakeRunner(legacy_catalog_posture_override={field: 1})
+
+    with pytest.raises(verifier.VerificationError) as caught:
+        run_success(runner)
+
+    assert caught.value.code == "legacy_catalog_privilege_posture_mismatch"
+    assert caught.value.check == "legacy_catalog_privileges"
+    assert SECRET_VALUE not in str(caught.value)
+
+
+def test_teleo_restore_catalog_and_behavioral_denial_are_both_exercised_on_legacy_database() -> None:
+    runner = FakeRunner()
+
+    receipt = run_success(runner)
+
+    legacy_catalog_call = next(
+        command
+        for command, _env, _timeout, _discard in runner.calls
+        if any(part == f"--command={verifier._legacy_catalog_privilege_posture_sql()}" for part in command)
+    )
+    assert any(f"dbname={verifier.LEGACY_DATABASE}" in part for part in legacy_catalog_call)
+    legacy_denial = next(
+        check for check in receipt["checks"]["negative_permissions"] if check["check"] == "legacy_teleo_restore_read"
+    )
+    assert legacy_denial == {
+        "check": "legacy_teleo_restore_read",
+        "expected_sqlstate": "42501",
+        "observed_sqlstate": "42501",
+        "result": "denied",
+    }
+
+
+def test_required_sqlstate_mismatch_fails_closed_without_secret_in_error() -> None:
+    runner = FakeRunner(sqlstate_override=("canonical_insert", "23505"))
+
+    with pytest.raises(verifier.VerificationError) as caught:
+        run_success(runner)
+
+    error = caught.value
+    assert error.code == "negative_permission_sqlstate_mismatch"
+    assert error.check == "canonical_insert"
+    assert error.expected_sqlstate == "42501"
+    assert error.observed_sqlstate == "23505"
+    assert SECRET_VALUE not in str(error)
+    assert SECRET_VALUE not in verifier.canonical_json(verifier.failure_receipt(RUN_ID, error))
+    assert_child_boundaries(runner)
+
+
+def test_missing_verbose_sqlstate_fails_closed_without_raw_stderr() -> None:
+    runner = FakeRunner(sqlstate_missing_for="forged_proposer_overload")
+
+    with pytest.raises(verifier.VerificationError) as caught:
+        run_success(runner)
+
+    error = caught.value
+    assert error.code == "negative_permission_sqlstate_missing"
+    assert error.expected_sqlstate == "42883"
+    assert error.observed_sqlstate == "missing"
+    assert SECRET_VALUE not in json.dumps(error.as_dict())
+
+
+def test_unexpected_permission_success_fails_closed_and_transaction_sql_has_rollback() -> None:
+    runner = FakeRunner(unexpected_success_for="proposal_update")
+
+    with pytest.raises(verifier.VerificationError) as caught:
+        run_success(runner)
+
+    assert caught.value.code == "negative_permission_unexpectedly_succeeded"
+    assert caught.value.observed_sqlstate == "success"
+    proposal_update = next(
+        check for check in verifier._negative_checks(RUN_ID, SOURCE_REF) if check.name == "proposal_update"
+    )
+    assert proposal_update.sql.startswith("begin;\n")
+    assert proposal_update.sql.endswith("\nrollback;")
+    assert SECRET_VALUE not in str(caught.value)
+
+
+@pytest.mark.parametrize("administrator_mode", ["success", "wrong-error"])
+def test_administrator_secret_must_be_exact_iam_denial_and_stdout_is_discarded(administrator_mode: str) -> None:
+    runner = FakeRunner(administrator_mode=administrator_mode)
+
+    with pytest.raises(verifier.VerificationError) as caught:
+        run_success(runner)
+
+    expected_code = (
+        "administrator_secret_unexpectedly_readable"
+        if administrator_mode == "success"
+        else "administrator_secret_denial_not_iam_permission"
+    )
+    assert caught.value.code == expected_code
+    assert SECRET_VALUE not in str(caught.value)
+    assert SECRET_VALUE not in verifier.canonical_json(verifier.failure_receipt(RUN_ID, caught.value))
+    assert runner.calls[-1][3] is True
+
+
+def test_scoped_secret_failure_never_repeats_command_output() -> None:
+    runner = FakeRunner(scoped_failure=True)
+
+    with pytest.raises(verifier.VerificationError) as caught:
+        run_success(runner)
+
+    assert caught.value.code == "scoped_secret_access_failed"
+    assert SECRET_VALUE not in str(caught.value)
+    assert SECRET_VALUE not in verifier.canonical_json(verifier.failure_receipt(RUN_ID, caught.value))
+    assert len(runner.calls) == 1
+
+
+@pytest.mark.parametrize(
+    "invalid",
+    ["short", "UPPERCASE-RUN", "contains_underscore", "contains.dot", " leading-space", "a" * 65],
+)
+def test_run_id_validation_is_strict(invalid: str) -> None:
+    with pytest.raises(ValueError, match="8-64 lowercase"):
+        verifier.validate_run_id(invalid)
+
+
+def test_wrong_identity_or_non_ssl_connection_fails_before_permission_probes() -> None:
+    runner = FakeRunner(identity_override={"ssl": False})
+
+    with pytest.raises(verifier.VerificationError) as caught:
+        run_success(runner)
+
+    assert caught.value.code == "private_ssl_identity_mismatch"
+    assert len(runner.calls) == 2
+    assert SECRET_VALUE not in str(caught.value)
+
+
+def test_optional_receipt_is_canonical_mode_0600_and_refuses_symlink(tmp_path: Path) -> None:
+    payload = {"z": 2, "a": {"safe": True}}
+    output = tmp_path / "receipt.json"
+
+    verifier.write_receipt(output, payload)
+
+    assert output.read_text(encoding="utf-8") == verifier.canonical_json(payload)
+    assert stat.S_IMODE(output.stat().st_mode) == 0o600
+    assert output.read_text(encoding="utf-8").startswith('{"a":')
+
+    target = tmp_path / "target.json"
+    target.write_text("untouched", encoding="utf-8")
+    symlink = tmp_path / "symlink.json"
+    symlink.symlink_to(target)
+    with pytest.raises(OSError):
+        verifier.write_receipt(symlink, payload)
+    assert target.read_text(encoding="utf-8") == "untouched"
+
+
+def test_subprocess_runner_discards_administrator_stdout_at_file_descriptor(monkeypatch: pytest.MonkeyPatch) -> None:
+    observed: dict[str, object] = {}
+
+    def fake_run(command: list[str], **kwargs: object) -> subprocess.CompletedProcess[str]:
+        observed["command"] = command
+        observed.update(kwargs)
+        return subprocess.CompletedProcess(command, 1, stdout=None, stderr="PERMISSION_DENIED")
+
+    monkeypatch.setattr(verifier.subprocess, "run", fake_run)
+
+    result = verifier.subprocess_runner([verifier.GCLOUD_BIN, "test"], os.environ, 3, True)
+
+    assert observed["stdout"] is subprocess.DEVNULL
+    assert observed["stdin"] is subprocess.DEVNULL
+    assert observed["stderr"] is subprocess.PIPE
+    assert result.stdout == ""
+    assert result.returncode == 1
--- a/tests/test_gcp_leoclean_service_environment.py
+++ b/tests/test_gcp_leoclean_service_environment.py
@ -0,0 +1,281 @@
+import json
+import os
+import subprocess
+import sys
+from collections.abc import Mapping
+from pathlib import Path
+
+import pytest
+
+from ops import verify_gcp_leoclean_service_environment as verifier
+
+
+def environment_block(environment: Mapping[str, str]) -> bytes:
+    return b"\0".join(f"{key}={value}".encode() for key, value in environment.items()) + b"\0"
+
+
+def test_all_expected_fields_pass_and_receipt_contains_no_values() -> None:
+    environment = verifier.expected_environment()
+    environment.update({"HOME": "/home/teleo", "LANG": "C.UTF-8"})
+
+    parsed = verifier.parse_environment(environment_block(environment))
+    validated = verifier.validate_environment(parsed)
+    receipt = {
+        "runtime_environment": "scoped",
+        "status": "pass",
+        "validated_fields": list(validated),
+    }
+    rendered = verifier.canonical_json(receipt)
+
+    assert validated == tuple(sorted(verifier.expected_environment()))
+    assert json.loads(rendered) == receipt
+    assert rendered == json.dumps(receipt, ensure_ascii=True, separators=(",", ":"), sort_keys=True) + "\n"
+    for value in verifier.expected_environment().values():
+        assert value not in rendered
+
+
+@pytest.mark.parametrize("field", sorted(verifier.expected_environment()))
+def test_each_expected_field_mismatch_fails_closed(field: str) -> None:
+    environment = verifier.expected_environment()
+    environment[field] = "wrong-value-that-is-not-a-secret"
+
+    with pytest.raises(verifier.VerificationError) as caught:
+        verifier.validate_environment(environment)
+
+    assert caught.value.code == "environment_mismatch"
+    assert caught.value.fields == (field,)
+
+
+@pytest.mark.parametrize(
+    ("field", "unsafe_value", "expected_code"),
+    [
+        ("TELEO_CLOUDSQL_USER", "postgres", "environment_mismatch"),
+        (
+            "TELEO_CLOUDSQL_PASSWORD_SECRET",
+            verifier.ADMINISTRATOR_PASSWORD_SECRET,
+            "administrator_secret_reference",
+        ),
+    ],
+)
+def test_later_dropin_effective_override_fails_without_outputting_value(
+    field: str,
+    unsafe_value: str,
+    expected_code: str,
+) -> None:
+    environment = verifier.expected_environment()
+    environment[field] = unsafe_value
+
+    with pytest.raises(verifier.VerificationError) as caught:
+        verifier.validate_environment(environment)
+
+    rendered = verifier.canonical_json(verifier.failure_receipt(caught.value))
+    assert caught.value.code == expected_code
+    assert unsafe_value not in rendered
+
+
+@pytest.mark.parametrize(
+    ("field", "safe_label"),
+    [
+        ("PGPASSWORD", "PG*"),
+        ("pgservice", "PG*"),
+        ("CLOUDSDK_CONFIG", "CLOUDSDK_*"),
+        ("CLOUDSDK_CORE_PROJECT", "CLOUDSDK_*"),
+        ("CLOUDSDK_AUTH_ACCESS_TOKEN", "CLOUDSDK_*"),
+        ("cloudsdk_auth_refresh_token", "CLOUDSDK_*"),
+        ("GOOGLE_APPLICATION_CREDENTIALS", "GOOGLE_APPLICATION_CREDENTIALS"),
+        ("LD_PRELOAD", "LD_*"),
+        ("LD_LIBRARY_PATH", "LD_*"),
+        ("ld_audit", "LD_*"),
+        ("BASH_ENV", "BASH_ENV"),
+        ("ENV", "ENV"),
+        ("BASH_FUNC_injected%%", "BASH_FUNC_*"),
+        ("PYTHONHOME", "PYTHON*"),
+        ("PYTHONPATH", "PYTHON*"),
+        ("PYTHONHTTPSVERIFY", "PYTHON*"),
+        ("pythonstartup", "PYTHON*"),
+        ("HTTP_PROXY", "HTTP_PROXY"),
+        ("https_proxy", "HTTPS_PROXY"),
+        ("ALL_PROXY", "ALL_PROXY"),
+        ("no_proxy", "NO_PROXY"),
+        ("SSL_CERT_FILE", "SSL_CERT_FILE"),
+        ("ssl_cert_dir", "SSL_CERT_DIR"),
+        ("REQUESTS_CA_BUNDLE", "REQUESTS_CA_BUNDLE"),
+        ("curl_ca_bundle", "CURL_CA_BUNDLE"),
+        ("SSLKEYLOGFILE", "SSLKEYLOGFILE"),
+    ],
+)
+def test_environment_file_broader_credentials_and_forbidden_fields_fail_closed(
+    field: str,
+    safe_label: str,
+) -> None:
+    environment = verifier.expected_environment()
+    injected_value = "sensitive-injected-value"
+    environment[field] = injected_value
+
+    with pytest.raises(verifier.VerificationError) as caught:
+        verifier.validate_environment(environment)
+
+    rendered = verifier.canonical_json(verifier.failure_receipt(caught.value))
+    assert caught.value.code == "forbidden_environment_fields"
+    assert caught.value.fields == (safe_label,)
+    assert injected_value not in rendered
+
+
+def test_arbitrary_forbidden_key_suffix_is_not_an_output_channel() -> None:
+    environment = verifier.expected_environment()
+    environment["PG_SECRET_MARKER"] = "not-output"
+
+    with pytest.raises(verifier.VerificationError) as caught:
+        verifier.validate_environment(environment)
+
+    rendered = verifier.canonical_json(verifier.failure_receipt(caught.value))
+    assert "PG_SECRET_MARKER" not in rendered
+    assert "PG*" in rendered
+
+
+def test_pythonunbuffered_is_the_only_allowed_python_runtime_tuning() -> None:
+    environment = verifier.expected_environment()
+    environment["PYTHONUNBUFFERED"] = "1"
+
+    assert verifier.validate_environment(environment) == tuple(sorted(verifier.expected_environment()))
+
+
+def test_bash_env_executes_before_a_script_but_effective_verifier_rejects_it(tmp_path: Path) -> None:
+    marker = "BASH_ENV_EXECUTED"
+    payload = tmp_path / "bash-env.sh"
+    payload.write_text(f"printf '{marker}\\n'\n", encoding="utf-8")
+    completed = subprocess.run(
+        ["/bin/bash", "-c", ":"],
+        env={"BASH_ENV": str(payload), "PATH": verifier.RUNTIME_PATH},
+        check=False,
+        capture_output=True,
+        text=True,
+    )
+    assert completed.returncode == 0
+    assert completed.stdout.strip() == marker
+
+    environment = verifier.expected_environment()
+    environment["BASH_ENV"] = str(payload)
+    with pytest.raises(verifier.VerificationError) as caught:
+        verifier.validate_environment(environment)
+    assert caught.value.fields == ("BASH_ENV",)
+
+
+def test_admin_secret_reference_in_any_value_fails_without_field_or_value_leak() -> None:
+    environment = verifier.expected_environment()
+    environment["UNRELATED"] = f"prefix/{verifier.ADMINISTRATOR_PASSWORD_SECRET}/suffix"
+
+    with pytest.raises(verifier.VerificationError) as caught:
+        verifier.validate_environment(environment)
+
+    rendered = verifier.canonical_json(verifier.failure_receipt(caught.value))
+    assert caught.value.code == "administrator_secret_reference"
+    assert verifier.ADMINISTRATOR_PASSWORD_SECRET not in rendered
+    assert "UNRELATED" not in rendered
+
+
+@pytest.mark.parametrize(
+    "raw",
+    [
+        b"A=1",
+        b"A=1\0\0",
+        b"A=1\0BROKEN\0",
+        b"=value\0",
+        b"A=1\0A=2\0",
+        b"A=\xff\0",
+        b"",
+    ],
+)
+def test_malformed_nul_environment_is_rejected(raw: bytes) -> None:
+    with pytest.raises(verifier.VerificationError) as caught:
+        verifier.parse_environment(raw)
+
+    assert caught.value.code == "environment_malformed"
+
+
+def test_parser_preserves_equals_inside_values() -> None:
+    assert verifier.parse_environment(b"A=one=two\0B=\0") == {"A": "one=two", "B": ""}
+
+
+@pytest.mark.parametrize("value", [0, -1, 1.5, "0", "01", "+1", "-3", "not-a-pid", True])
+def test_pid_must_be_a_positive_integer(value: object) -> None:
+    with pytest.raises(verifier.VerificationError) as caught:
+        verifier.validate_pid(value)  # type: ignore[arg-type]
+
+    assert caught.value.code == "invalid_pid"
+
+
+def test_cli_errors_are_canonical_sanitized_json_and_exit_one(capsys: pytest.CaptureFixture[str]) -> None:
+    secret_input = "not-a-pid-secret-marker"
+
+    returncode = verifier.main(["--pid", secret_input])
+
+    output = capsys.readouterr()
+    assert returncode == 1
+    assert output.err == ""
+    assert json.loads(output.out) == {"error": {"code": "invalid_pid"}, "status": "fail"}
+    assert secret_input not in output.out
+
+
+@pytest.mark.skipif(not sys.platform.startswith("linux"), reason="requires Linux /proc/PID/environ")
+def test_cli_reads_real_process_environment_and_detects_effective_conflict(
+    capsys: pytest.CaptureFixture[str],
+) -> None:
+    expected = verifier.expected_environment()
+    good_process = subprocess.Popen(
+        ["/bin/sleep", "30"],
+        env=expected,
+        stdin=subprocess.DEVNULL,
+        stdout=subprocess.DEVNULL,
+        stderr=subprocess.DEVNULL,
+    )
+    try:
+        assert verifier.main(["--pid", str(good_process.pid)]) == 0
+        good_output = capsys.readouterr()
+        assert good_output.err == ""
+        assert json.loads(good_output.out)["status"] == "pass"
+    finally:
+        good_process.terminate()
+        good_process.wait(timeout=5)
+
+    conflicting = dict(expected)
+    conflicting["TELEO_CLOUDSQL_USER"] = "postgres"
+    conflicting["GOOGLE_APPLICATION_CREDENTIALS"] = "/tmp/broader-credential.json"
+    bad_process = subprocess.Popen(
+        ["/bin/sleep", "30"],
+        env=conflicting,
+        stdin=subprocess.DEVNULL,
+        stdout=subprocess.DEVNULL,
+        stderr=subprocess.DEVNULL,
+    )
+    try:
+        assert verifier.main(["--pid", str(bad_process.pid)]) == 1
+        bad_output = capsys.readouterr()
+        receipt = json.loads(bad_output.out)
+        assert bad_output.err == ""
+        assert receipt == {
+            "error": {"code": "forbidden_environment_fields", "fields": ["GOOGLE_APPLICATION_CREDENTIALS"]},
+            "status": "fail",
+        }
+        assert "postgres" not in bad_output.out
+        assert "/tmp/broader-credential.json" not in bad_output.out
+    finally:
+        bad_process.terminate()
+        bad_process.wait(timeout=5)
+
+
+def test_unexpected_read_error_is_generic_and_does_not_echo_path(
+    monkeypatch: pytest.MonkeyPatch,
+    capsys: pytest.CaptureFixture[str],
+) -> None:
+    sensitive_marker = "sensitive-proc-read-detail"
+
+    def fail_read(_self: object) -> bytes:
+        raise OSError(sensitive_marker)
+
+    monkeypatch.setattr(verifier.Path, "read_bytes", fail_read)
+
+    assert verifier.main(["--pid", str(os.getpid())]) == 1
+    output = capsys.readouterr()
+    assert json.loads(output.out) == {"error": {"code": "internal_error"}, "status": "fail"}
+    assert sensitive_marker not in output.out
--- a/tests/test_hermes_leoclean_kb_bridge_source.py
+++ b/tests/test_hermes_leoclean_kb_bridge_source.py
@ -3,6 +3,7 @@
 from __future__ import annotations

 import ast
+import base64
 import contextlib
 import importlib.util
 import io
@ -64,6 +65,14 @@ def test_cloudsql_wrapper_supports_expected_review_gated_commands() -> None:
        assert command in cloudsql_text

    assert "status" in vps_text
+    assert "SCRIPT_DIR=${SCRIPT_PATH%/*}" in wrapper_text
+    assert 'SCRIPT_DIR="$(cd "$SCRIPT_DIR" && pwd)"' in wrapper_text
+    assert 'CLOUDSQL_TOOL="$SCRIPT_DIR/cloudsql_memory_tool.py"' in wrapper_text
+    assert wrapper_text.startswith("#!/bin/bash\n")
+    assert "exec /usr/bin/python3" in wrapper_text
+    assert "command -v psql" in wrapper_text
+    assert "gcloud" not in wrapper_text
+    assert '"gcloud"' not in cloudsql_text

    assert "kb_stage.kb_proposals" in cloudsql_text
    assert "canonical apply" in cloudsql_text.lower()
@ -95,7 +104,7 @@ def _install_wrapper_fixture(tmp_path: Path, *, missing: frozenset[str] = frozen
        target = shutil.which(name)
        assert target
        (fake_bin / name).symlink_to(target)
-    for name in ("psql", "gcloud"):
+    for name in ("psql",):
        if name in missing:
            continue
        executable = fake_bin / name
@ -146,7 +155,7 @@ def test_cloudsql_wrapper_auto_mode_never_falls_back_after_supported_command_fai
    assert "local" not in completed.stdout


-@pytest.mark.parametrize("missing", ["cloudsql-tool", "psql", "gcloud"])
+@pytest.mark.parametrize("missing", ["cloudsql-tool", "psql"])
 def test_cloudsql_wrapper_auto_mode_fails_closed_when_prerequisite_is_missing(tmp_path: Path, missing: str) -> None:
    wrapper, env = _install_wrapper_fixture(tmp_path, missing=frozenset({missing}))

@ -209,6 +218,72 @@ def test_bridge_source_does_not_commit_raw_secret_values() -> None:
        assert not re.search(pattern, combined), pattern


+def _runtime_connection_args(module, **overrides):
+    values = {
+        "credential_mode": "runtime",
+        "user": module.RUNTIME_DB_USER,
+        "password_secret": module.RUNTIME_PASSWORD_SECRET,
+        "project": module.RUNTIME_GCP_PROJECT,
+        "host": module.RUNTIME_CLOUDSQL_HOST,
+        "port": module.RUNTIME_CLOUDSQL_PORT,
+        "db": module.RUNTIME_CLOUDSQL_DB,
+        "canonical_db": module.RUNTIME_CLOUDSQL_DB,
+        "command": "status",
+    }
+    values.update(overrides)
+    return SimpleNamespace(**values)
+
+
+def _configure_runtime_environment(monkeypatch: pytest.MonkeyPatch) -> None:
+    for key in tuple(os.environ):
+        normalized_key = key.upper()
+        if (
+            normalized_key.startswith("PG")
+            or normalized_key.startswith("CLOUDSDK_")
+            or normalized_key == "GOOGLE_APPLICATION_CREDENTIALS"
+            or normalized_key in {"LD_PRELOAD", "PYTHONHOME", "PYTHONPATH"}
+            or normalized_key == "PROXY"
+            or normalized_key.endswith("_PROXY")
+            or normalized_key in {
+                "CURL_CA_BUNDLE",
+                "PYTHONHTTPSVERIFY",
+                "REQUESTS_CA_BUNDLE",
+                "SSL_CERT_DIR",
+                "SSL_CERT_FILE",
+                "SSLKEYLOGFILE",
+            }
+        ):
+            monkeypatch.delenv(key, raising=False)
+    monkeypatch.setenv("TELEO_GCP_METADATA_ONLY", "1")
+    monkeypatch.setenv("TELEO_CLOUDSQL_ENABLE_AUDIT_FALLBACK", "0")
+
+
+class _FakeHttpResponse:
+    def __init__(self, body: bytes, status: int = 200) -> None:
+        self.body = body
+        self.status = status
+
+    def __enter__(self):
+        return self
+
+    def __exit__(self, *_args) -> None:
+        return None
+
+    def getcode(self) -> int:
+        return self.status
+
+    def read(self, _limit: int) -> bytes:
+        return self.body
+
+
+def _runtime_http_bodies(module, password: bytes = b"scoped-runtime-password") -> list[bytes]:
+    return [
+        module.RUNTIME_SERVICE_ACCOUNT.encode("ascii"),
+        json.dumps({"access_token": "metadata-access-token", "token_type": "Bearer", "expires_in": 300}).encode(),
+        json.dumps({"payload": {"data": base64.b64encode(password).decode("ascii")}}).encode(),
+    ]
+
+
 def test_cloudsql_runtime_requires_the_exact_scoped_identity(monkeypatch: pytest.MonkeyPatch) -> None:
    module = _load_module(BRIDGE_DIR / "cloudsql_memory_tool.py")
    monkeypatch.delenv("PGPASSWORD", raising=False)
@ -249,17 +324,113 @@ def test_cloudsql_runtime_accepts_only_scoped_credentials_and_rejects_inherited_
    monkeypatch: pytest.MonkeyPatch,
 ) -> None:
    module = _load_module(BRIDGE_DIR / "cloudsql_memory_tool.py")
-    args = SimpleNamespace(
-        credential_mode="runtime",
-        user=module.RUNTIME_DB_USER,
-        password_secret=module.RUNTIME_PASSWORD_SECRET,
-    )
-    monkeypatch.delenv("PGPASSWORD", raising=False)
+    args = _runtime_connection_args(module)
+    _configure_runtime_environment(monkeypatch)

    module.validate_runtime_connection(args)

    monkeypatch.setenv("PGPASSWORD", "")
-    with pytest.raises(SystemExit, match="Refusing inherited PGPASSWORD"):
+    with pytest.raises(SystemExit, match="Refusing inherited credential, proxy, TLS, or PostgreSQL environment"):
+        module.validate_runtime_connection(args)
+
+
+@pytest.mark.parametrize(
+    ("name", "value"),
+    [
+        ("GOOGLE_APPLICATION_CREDENTIALS", "/tmp/ambient.json"),
+        ("google_application_credentials", "/tmp/ambient-lowercase.json"),
+        ("CLOUDSDK_CONFIG", "/tmp/gcloud"),
+        ("CLOUDSDK_AUTH_ACCESS_TOKEN", "ambient-token"),
+        ("cloudsdk_core_project", "attacker-project"),
+        ("cloudsdk_auth_access_token", "ambient-lowercase-token"),
+        ("PGHOST", "attacker.invalid"),
+        ("PGOPTIONS", "-c search_path=attacker"),
+        ("pgservice", "attacker-service"),
+        ("ld_preload", "/tmp/attacker.so"),
+        ("LD_LIBRARY_PATH", "/tmp/attacker-library"),
+        ("Ld_AuDiT", "/tmp/attacker-audit.so"),
+        ("BASH_ENV", "/tmp/attacker-bash-env"),
+        ("ENV", "/tmp/attacker-sh-env"),
+        ("BASH_FUNC_psql%%", "() { :; }"),
+        ("PythonHome", "/tmp/attacker-python"),
+        ("pythonpath", "/tmp/attacker-modules"),
+        ("PYTHONHTTPSVERIFY", "0"),
+        ("pythonstartup", "/tmp/attacker-startup.py"),
+        ("https_proxy", "http://attacker.invalid:8080"),
+        ("HtTp_PrOxY", "http://attacker.invalid:8080"),
+        ("ssl_cert_file", "/tmp/attacker.pem"),
+        ("SSL_CERT_DIR", "/tmp/attacker-certs"),
+        ("REQUESTS_CA_BUNDLE", "/tmp/attacker.pem"),
+        ("SSLKEYLOGFILE", "/tmp/attacker-tls-keys"),
+    ],
+)
+def test_cloudsql_runtime_rejects_ambient_auth_and_pg_environment(
+    monkeypatch: pytest.MonkeyPatch,
+    name: str,
+    value: str,
+) -> None:
+    module = _load_module(BRIDGE_DIR / "cloudsql_memory_tool.py")
+    args = _runtime_connection_args(module)
+    _configure_runtime_environment(monkeypatch)
+    monkeypatch.setenv(name, value)
+
+    with pytest.raises(SystemExit, match="Refusing inherited credential, proxy, TLS, or PostgreSQL environment"):
+        module.validate_runtime_connection(args)
+
+
+def test_cloudsql_runtime_allows_only_pythonunbuffered_runtime_tuning(
+    monkeypatch: pytest.MonkeyPatch,
+) -> None:
+    module = _load_module(BRIDGE_DIR / "cloudsql_memory_tool.py")
+    args = _runtime_connection_args(module)
+    _configure_runtime_environment(monkeypatch)
+    monkeypatch.setenv("PYTHONUNBUFFERED", "1")
+
+    module.validate_runtime_connection(args)
+
+
+def test_cloudsql_runtime_requires_explicit_metadata_only_mode(monkeypatch: pytest.MonkeyPatch) -> None:
+    module = _load_module(BRIDGE_DIR / "cloudsql_memory_tool.py")
+    args = _runtime_connection_args(module)
+    _configure_runtime_environment(monkeypatch)
+    monkeypatch.delenv("TELEO_GCP_METADATA_ONLY")
+
+    with pytest.raises(SystemExit, match="TELEO_GCP_METADATA_ONLY=1"):
+        module.validate_runtime_connection(args)
+
+
+@pytest.mark.parametrize(
+    ("field", "value", "message"),
+    [
+        ("project", "other-project", "project=teleo-501523"),
+        ("host", "127.0.0.1", "host=10.61.0.3"),
+        ("port", "6543", "port=5432"),
+        ("db", "teleo_kb", "db=teleo_canonical"),
+        ("canonical_db", "teleo_kb", "canonical_db=teleo_canonical"),
+    ],
+)
+def test_cloudsql_runtime_rejects_any_target_drift_before_credentials(
+    monkeypatch: pytest.MonkeyPatch,
+    field: str,
+    value: str,
+    message: str,
+) -> None:
+    module = _load_module(BRIDGE_DIR / "cloudsql_memory_tool.py")
+    args = _runtime_connection_args(module, **{field: value})
+    monkeypatch.delenv("PGPASSWORD", raising=False)
+    monkeypatch.setenv("TELEO_CLOUDSQL_ENABLE_AUDIT_FALLBACK", "0")
+
+    with pytest.raises(SystemExit, match=message):
+        module.validate_runtime_connection(args)
+
+
+def test_cloudsql_runtime_rejects_audit_fallback(monkeypatch: pytest.MonkeyPatch) -> None:
+    module = _load_module(BRIDGE_DIR / "cloudsql_memory_tool.py")
+    args = _runtime_connection_args(module)
+    monkeypatch.delenv("PGPASSWORD", raising=False)
+    monkeypatch.setenv("TELEO_CLOUDSQL_ENABLE_AUDIT_FALLBACK", "1")
+
+    with pytest.raises(SystemExit, match="AUDIT_FALLBACK=0"):
        module.validate_runtime_connection(args)


@ -290,33 +461,44 @@ def test_cloudsql_clone_mode_is_read_only_and_bound_to_one_disposable_database(
        module.validate_runtime_connection(args)


-def test_cloudsql_psql_uses_only_explicit_pg_environment_fields(monkeypatch: pytest.MonkeyPatch) -> None:
+def test_cloudsql_clone_mode_never_resolves_a_password_secret_argument(monkeypatch: pytest.MonkeyPatch) -> None:
    module = _load_module(BRIDGE_DIR / "cloudsql_memory_tool.py")
    args = SimpleNamespace(
-        credential_mode="runtime",
-        user=module.RUNTIME_DB_USER,
-        password_secret=module.RUNTIME_PASSWORD_SECRET,
-        host="10.61.0.3",
-        port="5432",
-        db="teleo_canonical",
-        canonical_db="teleo_canonical",
-        project="teleo-501523",
+        credential_mode="clone-readonly",
+        user="postgres",
+        password_secret="gcp-teleo-pgvector-standby-postgres-password",
+        canonical_db="teleo_clone_canary_123",
+        db="teleo_clone_canary_123",
        command="status",
    )
    monkeypatch.delenv("PGPASSWORD", raising=False)
-    monkeypatch.setenv("PGHOST", "attacker.invalid")
-    monkeypatch.setenv("PGSERVICE", "untrusted-service")
-    monkeypatch.setenv("PGPASSFILE", "/tmp/untrusted-pgpass")
-    monkeypatch.setenv("PGOPTIONS", "-c search_path=attacker")
+    monkeypatch.setenv("PGOPTIONS", module.CLONE_READ_ONLY_PGOPTIONS)
+    monkeypatch.setattr(
+        module.subprocess,
+        "run",
+        lambda *_args, **_kwargs: pytest.fail("a password-secret argument must never launch a credential helper"),
+    )
+
+    with pytest.raises(SystemExit, match="requires an explicit user and inherited test credential"):
+        module.password(args)
+
+
+def test_cloudsql_psql_uses_only_explicit_pg_environment_fields(monkeypatch: pytest.MonkeyPatch) -> None:
+    module = _load_module(BRIDGE_DIR / "cloudsql_memory_tool.py")
+    args = _runtime_connection_args(module)
+    _configure_runtime_environment(monkeypatch)
+    monkeypatch.setenv("HOME", "/tmp/untrusted-home")
+    monkeypatch.setenv("LANG", "attacker-locale")
+    monkeypatch.setenv("SHELL", "/tmp/untrusted-shell")
+    monkeypatch.setenv("UNRELATED_AMBIENT_VALUE", "must-not-reach-psql")
    captured: dict[str, object] = {}

    def fake_run(command, **kwargs):
-        if command[0] == "gcloud":
-            return SimpleNamespace(returncode=0, stdout="scoped-runtime-password\n", stderr="")
        captured["command"] = command
        captured["kwargs"] = kwargs
        return SimpleNamespace(returncode=0, stdout="ok\n", stderr="")

+    monkeypatch.setattr(module, "runtime_password_from_metadata", lambda: "scoped-runtime-password")
    monkeypatch.setattr(module.subprocess, "run", fake_run)

    assert module.run_psql(args, "select 1;") == "ok\n"
@ -324,16 +506,279 @@ def test_cloudsql_psql_uses_only_explicit_pg_environment_fields(monkeypatch: pyt
    kwargs = captured["kwargs"]
    assert isinstance(kwargs, dict)
    env = kwargs["env"]
-    assert env["PGHOST"] == "10.61.0.3"
-    assert env["PGPORT"] == "5432"
-    assert env["PGDATABASE"] == "teleo_canonical"
-    assert env["PGUSER"] == module.RUNTIME_DB_USER
-    assert env["PGSSLMODE"] == "require"
-    assert env["PGCONNECT_TIMEOUT"] == "8"
-    assert env["PGPASSWORD"] == "scoped-runtime-password"
-    assert "PGOPTIONS" not in env
-    assert "PGSERVICE" not in env
-    assert "PGPASSFILE" not in env
+    assert env == {
+        "PATH": "/usr/bin:/bin",
+        "PGHOST": "10.61.0.3",
+        "PGPORT": "5432",
+        "PGDATABASE": "teleo_canonical",
+        "PGUSER": module.RUNTIME_DB_USER,
+        "PGSSLMODE": "require",
+        "PGCONNECT_TIMEOUT": "8",
+        "PGPASSWORD": "scoped-runtime-password",
+    }
+
+
+def test_cloudsql_runtime_metadata_and_secret_requests_are_exact_and_silent(
+    monkeypatch: pytest.MonkeyPatch,
+    capsys: pytest.CaptureFixture[str],
+) -> None:
+    module = _load_module(BRIDGE_DIR / "cloudsql_memory_tool.py")
+    args = _runtime_connection_args(module)
+    _configure_runtime_environment(monkeypatch)
+    bodies = _runtime_http_bodies(module)
+    requests: list[tuple[str, str, dict[str, str], float]] = []
+
+    def fake_urlopen(request, *, timeout):
+        requests.append(
+            (
+                request.full_url,
+                request.get_method(),
+                {key.lower(): value for key, value in request.header_items()},
+                timeout,
+            )
+        )
+        return _FakeHttpResponse(bodies.pop(0))
+
+    monkeypatch.setattr(module.RUNTIME_HTTP_OPENER, "open", fake_urlopen)
+
+    assert module.password(args) == "scoped-runtime-password"
+    assert module.GCE_METADATA_EMAIL_URL == (
+        "http://169.254.169.254/computeMetadata/v1/instance/service-accounts/default/email"
+    )
+    assert module.GCE_METADATA_TOKEN_URL == (
+        "http://169.254.169.254/computeMetadata/v1/instance/service-accounts/default/token"
+    )
+    assert requests == [
+        (
+            module.GCE_METADATA_EMAIL_URL,
+            "GET",
+            {"metadata-flavor": "Google"},
+            module.HTTP_TIMEOUT_SECONDS,
+        ),
+        (
+            module.GCE_METADATA_TOKEN_URL,
+            "GET",
+            {"metadata-flavor": "Google"},
+            module.HTTP_TIMEOUT_SECONDS,
+        ),
+        (
+            module.RUNTIME_SECRET_ACCESS_URL,
+            "GET",
+            {"accept": "application/json", "authorization": "Bearer metadata-access-token"},
+            module.HTTP_TIMEOUT_SECONDS,
+        ),
+    ]
+    assert capsys.readouterr() == ("", "")
+
+
+def test_cloudsql_runtime_http_opener_disables_proxies_and_redirects() -> None:
+    module = _load_module(BRIDGE_DIR / "cloudsql_memory_tool.py")
+    proxy_handlers = [
+        handler for handler in module.RUNTIME_HTTP_OPENER.handlers if isinstance(handler, module.urllib.request.ProxyHandler)
+    ]
+    redirect_handlers = [
+        handler
+        for handler in module.RUNTIME_HTTP_OPENER.handlers
+        if isinstance(handler, module.urllib.request.HTTPRedirectHandler)
+    ]
+
+    # An empty ProxyHandler suppresses build_opener's environment-backed default;
+    # urllib omits the empty handler itself from the final chain.
+    assert proxy_handlers == []
+    assert module.RUNTIME_PROXY_HANDLER.proxies == {}
+    assert len(redirect_handlers) == 1
+    assert type(redirect_handlers[0]) is module._RejectRedirectHandler
+
+
+def test_cloudsql_runtime_rejects_wrong_metadata_service_account_before_token(
+    monkeypatch: pytest.MonkeyPatch,
+) -> None:
+    module = _load_module(BRIDGE_DIR / "cloudsql_memory_tool.py")
+    args = _runtime_connection_args(module)
+    _configure_runtime_environment(monkeypatch)
+    calls: list[str] = []
+
+    def fake_urlopen(request, *, timeout):
+        assert timeout == module.HTTP_TIMEOUT_SECONDS
+        calls.append(request.full_url)
+        return _FakeHttpResponse(b"unexpected-sa@teleo-501523.iam.gserviceaccount.com")
+
+    monkeypatch.setattr(module.RUNTIME_HTTP_OPENER, "open", fake_urlopen)
+
+    with pytest.raises(SystemExit, match="did not match the required service account"):
+        module.password(args)
+    assert calls == [module.GCE_METADATA_EMAIL_URL]
+
+
+@pytest.mark.parametrize(
+    "token_body",
+    [
+        b"not-json",
+        b"[]",
+        b'{"access_token":"token","token_type":"Basic","expires_in":300}',
+        b'{"access_token":"token with spaces","token_type":"Bearer","expires_in":300}',
+        b'{"access_token":"token","token_type":"Bearer","expires_in":0}',
+        b'{"access_token":"one","access_token":"two","token_type":"Bearer","expires_in":300}',
+    ],
+)
+def test_cloudsql_runtime_rejects_malformed_metadata_tokens_without_leaking_them(
+    monkeypatch: pytest.MonkeyPatch,
+    token_body: bytes,
+) -> None:
+    module = _load_module(BRIDGE_DIR / "cloudsql_memory_tool.py")
+    args = _runtime_connection_args(module)
+    _configure_runtime_environment(monkeypatch)
+    bodies = [module.RUNTIME_SERVICE_ACCOUNT.encode("ascii"), token_body]
+    monkeypatch.setattr(
+        module.RUNTIME_HTTP_OPENER,
+        "open",
+        lambda _request, *, timeout: _FakeHttpResponse(bodies.pop(0)),
+    )
+
+    with pytest.raises(SystemExit, match="Runtime metadata token response was invalid") as captured:
+        module.password(args)
+    assert "token with spaces" not in str(captured.value)
+
+
+@pytest.mark.parametrize(
+    "secret_body",
+    [
+        b"not-json",
+        b"[]",
+        b"{}",
+        b'{"payload":{"data":"%%%"}}',
+        json.dumps({"payload": {"data": base64.b64encode(b"x" * 4097).decode("ascii")}}).encode(),
+        json.dumps({"payload": {"data": base64.b64encode(b"line1\nline2").decode("ascii")}}).encode(),
+        json.dumps({"payload": {"data": base64.b64encode(b"line1\rline2").decode("ascii")}}).encode(),
+        json.dumps({"payload": {"data": base64.b64encode(b"nul\x00byte").decode("ascii")}}).encode(),
+    ],
+)
+def test_cloudsql_runtime_rejects_malformed_secret_payloads_without_leaking_them(
+    monkeypatch: pytest.MonkeyPatch,
+    secret_body: bytes,
+) -> None:
+    module = _load_module(BRIDGE_DIR / "cloudsql_memory_tool.py")
+    args = _runtime_connection_args(module)
+    _configure_runtime_environment(monkeypatch)
+    bodies = _runtime_http_bodies(module)
+    bodies[-1] = secret_body
+    monkeypatch.setattr(
+        module.RUNTIME_HTTP_OPENER,
+        "open",
+        lambda _request, *, timeout: _FakeHttpResponse(bodies.pop(0)),
+    )
+
+    with pytest.raises(SystemExit, match=r"Scoped runtime secret .* invalid") as captured:
+        module.password(args)
+    assert secret_body.decode("utf-8", errors="ignore") not in str(captured.value)
+
+
+def test_cloudsql_runtime_admin_secret_is_impossible_through_arguments(
+    monkeypatch: pytest.MonkeyPatch,
+) -> None:
+    module = _load_module(BRIDGE_DIR / "cloudsql_memory_tool.py")
+    args = _runtime_connection_args(module, password_secret="gcp-teleo-pgvector-standby-postgres-password")
+    _configure_runtime_environment(monkeypatch)
+    monkeypatch.setattr(
+        module.RUNTIME_HTTP_OPENER,
+        "open",
+        lambda *_args, **_kwargs: pytest.fail("metadata must not be queried for an admin secret argument"),
+    )
+
+    with pytest.raises(SystemExit, match="requires scoped password secret"):
+        module.password(args)
+
+
+def test_cloudsql_runtime_http_and_psql_failures_never_echo_credentials(
+    monkeypatch: pytest.MonkeyPatch,
+) -> None:
+    module = _load_module(BRIDGE_DIR / "cloudsql_memory_tool.py")
+    args = _runtime_connection_args(module)
+    _configure_runtime_environment(monkeypatch)
+    dummy = "DUMMY-RUNTIME-SECRET-DO-NOT-LEAK"
+
+    def failed_urlopen(_request, *, timeout):
+        raise RuntimeError(f"provider echoed {dummy}")
+
+    monkeypatch.setattr(module.RUNTIME_HTTP_OPENER, "open", failed_urlopen)
+    with pytest.raises(SystemExit) as http_error:
+        module.password(args)
+    assert dummy not in str(http_error.value)
+
+    monkeypatch.setattr(module, "runtime_password_from_metadata", lambda: dummy)
+    monkeypatch.setattr(
+        module.subprocess,
+        "run",
+        lambda *_args, **_kwargs: SimpleNamespace(returncode=2, stdout=dummy, stderr=dummy),
+    )
+    with pytest.raises(SystemExit, match="Cloud SQL query failed with exit status 2") as psql_error:
+        module.run_psql(args, "select 1;")
+    assert dummy not in str(psql_error.value)
+
+
+def test_cloudsql_runtime_read_marker_binds_database_user_private_server_and_ssl(
+    monkeypatch: pytest.MonkeyPatch,
+) -> None:
+    module = _load_module(BRIDGE_DIR / "cloudsql_memory_tool.py")
+    args = _runtime_connection_args(module)
+    marker = {
+        "database": module.RUNTIME_CLOUDSQL_DB,
+        "database_user": module.RUNTIME_DB_USER,
+        "server_addr": module.RUNTIME_CLOUDSQL_HOST,
+        "server_port": int(module.RUNTIME_CLOUDSQL_PORT),
+        "ssl": True,
+        "ssl_version": "TLSv1.3",
+        "system_identifier": "system-id",
+        "wal_lsn": "0/1",
+    }
+    captured: dict[str, object] = {}
+
+    def fake_psql_json_lines(_args, sql, db=None):
+        captured["sql"] = sql
+        captured["db"] = db
+        return [marker]
+
+    monkeypatch.setattr(module, "psql_json_lines", fake_psql_json_lines)
+
+    assert module.database_read_marker(args) == marker
+    assert captured["db"] == module.RUNTIME_CLOUDSQL_DB
+    assert "inet_server_addr()" in str(captured["sql"])
+    assert "pg_stat_ssl" in str(captured["sql"])
+
+
+@pytest.mark.parametrize(
+    ("field", "value", "message"),
+    [
+        ("database", "teleo_kb", "unexpected database identity"),
+        ("database_user", "postgres", "unexpected database identity"),
+        ("server_addr", "127.0.0.1", "unexpected server address"),
+        ("server_port", 6543, "unexpected server port"),
+        ("ssl", False, "encrypted connection"),
+    ],
+)
+def test_cloudsql_runtime_read_marker_rejects_wrong_live_identity(
+    monkeypatch: pytest.MonkeyPatch,
+    field: str,
+    value: object,
+    message: str,
+) -> None:
+    module = _load_module(BRIDGE_DIR / "cloudsql_memory_tool.py")
+    args = _runtime_connection_args(module)
+    marker = {
+        "database": module.RUNTIME_CLOUDSQL_DB,
+        "database_user": module.RUNTIME_DB_USER,
+        "server_addr": module.RUNTIME_CLOUDSQL_HOST,
+        "server_port": int(module.RUNTIME_CLOUDSQL_PORT),
+        "ssl": True,
+        "ssl_version": "TLSv1.3",
+        "system_identifier": "system-id",
+        "wal_lsn": "0/1",
+    }
+    marker[field] = value
+    monkeypatch.setattr(module, "psql_json_lines", lambda *_args, **_kwargs: [marker])
+
+    with pytest.raises(SystemExit, match=message):
+        module.database_read_marker(args)


 def test_cloudsql_proposal_calls_leave_leo_identity_to_the_database(monkeypatch: pytest.MonkeyPatch) -> None:
@ -390,6 +835,7 @@ def test_gcp_runtime_role_uses_one_narrow_staging_function() -> None:
    assert "can_insert_proposals_directly" in sql
    assert "can_create_database_objects" in sql
    assert "can_create_temp_objects" in sql
+    assert "can_connect_legacy_database" in sql
    assert "unexpectedly has database CREATE" in sql
    assert "REVOKE TEMP FROM PUBLIC would be a" in sql
    assert "can execute unexpected SECURITY DEFINER functions" in sql
@ -407,6 +853,15 @@ def test_gcp_runtime_role_uses_one_narrow_staging_function() -> None:
    )
    assert "grant update" not in sql.lower()
    assert "grant delete" not in sql.lower()
+    assert "create role leoclean_kb_runtime nologin" in sql.lower()
+    disable_statement = "alter role leoclean_kb_runtime\n  with nologin nosuperuser"
+    password_statement = "alter role leoclean_kb_runtime password"
+    assert sql.lower().index(disable_statement) < sql.lower().index(password_statement)
+    assert sql.lower().index(disable_statement) < sql.index("\\getenv runtime_password")
+    assert sql.index("\\getenv runtime_password") < sql.lower().index(password_statement)
+    assert sql.lower().index("with nologin nosuperuser") < sql.index("\\connect teleo_kb")
+    assert sql.index("\\connect teleo_kb") < sql.lower().rindex("with login nosuperuser")
+    assert "leoclean_kb_runtime final login attributes are unsafe" in sql


 def _load_module(path: Path):
--- a/tests/test_teleo_agent_systemd.py
+++ b/tests/test_teleo_agent_systemd.py
@ -187,15 +187,60 @@ def test_gcp_runtime_sync_is_source_bound_and_scoped():
    assert 'DROPIN_NAME="10-cloudsql-memory.conf"' in script
    assert "20-canonical-kb.conf" not in script
    assert "sha256sum" in script
+    assert "--preflight-only" in script
    assert "--restart" in script
-    assert 'python3 "$tool_path" status --format json --redacted' in script
+    assert '/usr/bin/python3 "$tool_path" status --format json --redacted' in script
    assert "sa-teleo-prod-vm@teleo-501523.iam.gserviceaccount.com" in script
-    assert "metadata.google.internal/computeMetadata/v1/instance/service-accounts/default/email" in script
-    assert "env -u PGPASSWORD" in script
-    assert 'run_scoped_status pre "$remote_tmp/$TOOL_REL"' in script
-    assert 'run_scoped_status post "$profile_bin/cloudsql_memory_tool.py"' in script
+    assert "169.254.169.254/computeMetadata/v1/instance/service-accounts/default/email" in script
+    assert "ProxyHandler({})" in script
+    assert "env -i" in script
+    assert 'run_scoped_status pre "$payload_dir/$TOOL_REL"' in script
+    assert 'run_permission_verifier pre "$payload_dir/$PERMISSION_VERIFIER_REL"' in script
+    assert 'sudo -n -u teleo mkdir -p -- "$receipt_dir"' in script
+    assert 'if [ "$PREFLIGHT_ONLY" = true ]; then' in script
+    assert "run_service_wrapper_status post" in script
+    assert "run_service_wrapper_status verify" in script
+    assert '"$SERVICE_PROFILE_BIN/teleo-kb" status --format json --redacted' in script
+    wrapper_probe = script.split("run_service_wrapper_status() {", maxsplit=1)[1].split(
+        "\n}\n\nservice_fingerprint", maxsplit=1
+    )[0]
+    assert 'nsenter -t "$main_pid" -m --env' in wrapper_probe
+    assert "/usr/bin/setpriv" in wrapper_probe
+    assert "--reuid=teleo" in wrapper_probe
+    assert "TELEO_CLOUDSQL_" not in wrapper_probe
+    assert "/usr/bin/env -i" not in wrapper_probe
+    assert 'run_permission_verifier post "$runtime_bin/verify_gcp_leoclean_runtime_permissions.py"' in script
+    assert 'SERVICE_ENV_VERIFIER_REL="ops/verify_gcp_leoclean_service_environment.py"' in script
+    assert 'assert_runtime_environment "$runtime_bin/verify_gcp_leoclean_service_environment.py"' in script
+    assert 'assert_runtime_environment "$REMOTE_RUNTIME_BIN/verify_gcp_leoclean_service_environment.py"' in script
+    assert "REMOTE_CLOUDSDK_CONFIG" not in script
+    assert "--property=DropInPaths" in script
+    assert "--property=EnvironmentFiles" in script
+    assert "Service has an effective EnvironmentFile" in script
+    assert "Service has a later drop-in" in script
+    assert "assert_administrator_secret_denied" in script
+    assert '"stdout_discarded": True' in script
+    assert '"credential_context": "systemd_main_pid_environment"' in script
+    administrator_probe = script.split("assert_administrator_secret_denied() {", maxsplit=1)[1].split(
+        "\n}\n\nrun_scoped_status", maxsplit=1
+    )[0]
+    assert 'nsenter -t "$main_pid" -m --env' in administrator_probe
+    assert "/usr/bin/setpriv" in administrator_probe
+    assert "env -i" not in administrator_probe
+    assert 'preflight_service_before="$(service_fingerprint)"' in script
+    assert 'assert_service_fingerprint "$preflight_service_before"' in script
    assert "backup_path" in script
+    assert "backup_directory_state" in script
    assert "restore_path" in script
+    assert "restore_directory_state" in script
+    assert 'runtime_grandparent="$(dirname "$runtime_parent")"' in script
+    assert 'runtime_anchor="$(dirname "$runtime_grandparent")"' in script
+    assert 'dropin_parent="$(dirname "$dropin_dir")"' in script
+    assert 'backup_directory_state "$runtime_grandparent" runtime_grandparent' in script
+    assert 'restore_directory_state "$runtime_grandparent" runtime_grandparent' in script
+    assert 'sudo test -d "$runtime_anchor"' in script
+    assert 'sudo test -d "$dropin_parent"' in script
+    assert 'sudo rmdir -- "$target"' in script
    assert "rollback_runtime" in script
    assert "trap 'on_exit $?' EXIT" in script
    assert 'backup_path "$dropin_dir/$DROPIN_NAME" dropin' in script
@ -205,13 +250,303 @@ def test_gcp_runtime_sync_is_source_bound_and_scoped():
    assert 'sub_state" != "running"' in script
    assert 'sudo systemctl stop "$SERVICE"' in script
    assert 'sudo systemctl start "$SERVICE"' in script
+    assert 'REMOTE_RUNTIME_BIN="${REMOTE_RUNTIME_BIN:-/usr/local/libexec/livingip/leoclean-kb}"' in script
+    assert 'sudo install -d -o root -g root -m 0755 "$runtime_parent"' in script
+    assert 'sudo install -d -o root -g root -m 0755 "$runtime_bin"' in script
+    assert 'remote_tmp="$(sudo mktemp -d /var/tmp/teleo-gcp-leoclean-runtime.XXXXXX)"' in script
+    assert 'sudo install -d -o root -g root -m 0755 "$payload_dir"' in script
+    assert 'sudo install -d -o root -g root -m 0700 "$backup_dir"' in script
+    assert 'sudo install -d -o teleo -g teleo -m 0700 "$work_dir"' in script
+    assert "sudo tar --no-same-owner --no-same-permissions" in script
+    assert 'sudo chown -R root:root "$payload_dir"' in script
+    assert 'sudo find "$payload_dir" -type d -exec chmod 0555 {} +' in script
+    assert 'sudo find "$payload_dir" -type l -print -quit' in script
+    assert 'sudo -n -u teleo test ! -w "$payload_dir"' in script
+    assert 'sudo -n -u teleo test ! -w "$backup_dir"' in script
+    assert 'sudo touch "$backup_dir/$name.present"' in script
+    assert 'sudo test -f "$backup_dir/$name.present"' in script
+    assert 'sudo install -o root -g root -m 0755 "$payload_dir/$WRAPPER_REL" "$wrapper_stage"' in script
+    assert 'sudo install -o root -g root -m 0755 "$payload_dir/$TOOL_REL" "$tool_stage"' in script
+    assert (
+        'sudo install -o root -g root -m 0755 "$payload_dir/$PERMISSION_VERIFIER_REL" '
+        '"$permission_verifier_stage"' in script
+    )
+    assert (
+        'sudo install -o root -g root -m 0755 "$payload_dir/$SERVICE_ENV_VERIFIER_REL" '
+        '"$service_env_verifier_stage"' in script
+    )
+    assert 'assert_installed_files\nsudo systemctl daemon-reload' in script
+    assert 'tar -C "$remote_tmp" -xf -' not in script
+    assert 'mkdir -p "$backup_dir"' not in script
+    assert 'for protected_file in \\\n    "$wrapper" \\' in script
+    assert '"$permission_verifier" \\' in script
+    assert '"$service_env_verifier" \\' in script
+    assert 'sudo -n -u teleo test ! -w "$protected_file"' in script
+    assert 'for protected_dir in \\\n    /usr \\' in script
+    assert "/usr/local/libexec/livingip" in script
+    assert 'sudo -n -u teleo test ! -w "$protected_dir"' in script
+    assert 'for executable_dir in \\\n    /usr/local/sbin \\' in script
+    assert 'sudo stat -Lc \'%U:%G\' "$executable_dir"' in script
+    assert 'sudo -n -u teleo test ! -w "$executable_dir"' in script
+    assert 'for protected_file in /bin/bash /usr/bin/curl /usr/bin/python3' in script
+    assert '/usr/bin/curl -q --noproxy' in script
+    assert 'test "$(sudo cat "$revision")" = "$SOURCE_REVISION"' in script
+    assert 'assert_existing_root_directory "$existing_directory"' in script
+    assert 'assert_existing_root_file "$existing_file"' in script
+    assert 'validate_restored_path "$runtime_bin/teleo-kb" wrapper' in script
+    assert 'validate_restored_directory "$runtime_bin" runtime_bin' in script
+    rollback = script.split("rollback_runtime() {", maxsplit=1)[1].split("\n}\n\non_exit()", maxsplit=1)[0]
+    assert rollback.index("validate_restored_path") < rollback.index("systemctl daemon-reload")
+    assert rollback.index("systemctl daemon-reload") < rollback.index('systemctl start "$SERVICE"')
+    assert rollback.count('if [ "$rollback_rc" -eq 0 ]; then') >= 3
+    deploy_tail = script.split("mutation_started=true", maxsplit=1)[1]
+    assert deploy_tail.index("assert_installed_files") < deploy_tail.index("systemctl daemon-reload")
+    assert deploy_tail.index("systemctl daemon-reload") < deploy_tail.index("assert_unit_configuration")
+    assert deploy_tail.index("assert_unit_configuration") < deploy_tail.index('systemctl start "$SERVICE"')
+    for install_line in (
+        'sudo install -o root -g root -m 0755 "$payload_dir/$WRAPPER_REL"',
+        'sudo install -o root -g root -m 0755 "$payload_dir/$TOOL_REL"',
+        'sudo install -o root -g root -m 0755 "$payload_dir/$PERMISSION_VERIFIER_REL"',
+        'sudo install -o root -g root -m 0755 "$payload_dir/$SERVICE_ENV_VERIFIER_REL"',
+        'sudo install -o root -g root -m 0644 "$payload_dir/$DROPIN_REL"',
+    ):
+        assert install_line in deploy_tail
+    assert 'sudo install -o root -g root -m 0755 "$work_dir/' not in script
+    assert 'nsenter -t "$main_pid" -m -- sha256sum "$SERVICE_PROFILE_BIN/teleo-kb"' in script
+    assert 'findmnt -T "$SERVICE_PROFILE_BIN"' in script
+    assert 'findmnt -M "$SERVICE_HERMES_ROOT"' in script
+    assert 'findmnt -M "$SERVICE_PROFILE_ROOT/state"' in script
+    assert 'findmnt -M "$SERVICE_PROFILE_ROOT/workspace"' in script
+    assert "cap_sys_admin" in script
+    assert '"current_tier": "T3_live_readonly"' in script
+    assert '"status": "pass"' in script
    assert "UnsetEnvironment=PGPASSWORD" in dropin
-    assert "RuntimeDirectory=leoclean-gcp-prod-parallel" in dropin
-    assert "RuntimeDirectoryMode=0700" in dropin
-    assert "Environment=CLOUDSDK_CONFIG=/run/leoclean-gcp-prod-parallel" in dropin
+    assert "UnsetEnvironment=GOOGLE_APPLICATION_CREDENTIALS CLOUDSDK_CONFIG" in dropin
+    assert "UnsetEnvironment=BASH_ENV ENV BASHOPTS SHELLOPTS" in dropin
+    assert "UnsetEnvironment=LD_PRELOAD LD_LIBRARY_PATH LD_AUDIT" in dropin
+    assert "UnsetEnvironment=PYTHONHOME PYTHONPATH PYTHONSTARTUP PYTHONINSPECT" in dropin
+    assert "UnsetEnvironment=HTTP_PROXY HTTPS_PROXY ALL_PROXY NO_PROXY" in dropin
+    assert "UnsetEnvironment=SSL_CERT_FILE SSL_CERT_DIR REQUESTS_CA_BUNDLE CURL_CA_BUNDLE SSLKEYLOGFILE" in dropin
+    assert (
+        "BindReadOnlyPaths=/usr/local/libexec/livingip/leoclean-kb:/home/teleo/.hermes/profiles/leoclean/bin" in dropin
+    )
+    assert "ReadOnlyPaths=/home/teleo/.hermes" in dropin
+    assert (
+        "ReadWritePaths=/home/teleo/.hermes/profiles/leoclean/state "
+        "/home/teleo/.hermes/profiles/leoclean/workspace" in dropin
+    )
+    assert "CapabilityBoundingSet=~CAP_SYS_ADMIN" in dropin
+    assert "RuntimeDirectory=" not in dropin
+    assert "Environment=CLOUDSDK_" not in dropin
+    assert "Environment=PATH=/usr/local/sbin:/usr/local/bin:/usr/sbin:/usr/bin:/sbin:/bin" in dropin
    assert "TELEO_KB_MODE=cloudsql" in dropin
+    assert "TELEO_GCP_METADATA_ONLY=1" in dropin
    assert "TELEO_CLOUDSQL_USER=leoclean_kb_runtime" in dropin
    assert "gcp-teleo-pgvector-standby-leoclean-kb-runtime-password" in dropin
    assert "TELEO_CLOUDSQL_ENABLE_AUDIT_FALLBACK=0" in dropin
    assert not any(line.startswith("Environment=PGPASSWORD") for line in dropin.splitlines())
    assert "gcp-teleo-pgvector-standby-postgres-password" not in dropin
+
+
+def test_gcp_runtime_embedded_remote_programs_are_bash_syntax_valid() -> None:
+    script = (REPO_ROOT / "deploy" / "sync-gcp-leoclean-runtime.sh").read_text()
+    blocks: dict[str, str] = {}
+
+    for variable in ("remote_helpers", "verify_body", "sync_body"):
+        marker = f"{variable}=$(cat <<'REMOTE'\n"
+        assert script.count(marker) == 1
+        start = script.index(marker) + len(marker)
+        end = script.index("\nREMOTE\n)", start)
+        blocks[variable] = script[start:end]
+
+    for name, body in (
+        *blocks.items(),
+        ("composed_verify", blocks["remote_helpers"] + "\n" + blocks["verify_body"]),
+        ("composed_sync", blocks["remote_helpers"] + "\n" + blocks["sync_body"]),
+    ):
+        completed = subprocess.run(
+            ["bash", "-n"],
+            input=body,
+            capture_output=True,
+            check=False,
+            text=True,
+        )
+        assert completed.returncode == 0, f"{name}: {completed.stderr}"
+
+    embedded_python = [part.split("\nPY", maxsplit=1)[0] for part in blocks["remote_helpers"].split("<<'PY'\n")[1:]]
+    assert len(embedded_python) == 2
+    for index, body in enumerate(embedded_python):
+        completed = subprocess.run(
+            ["python3", "-c", "import sys; compile(sys.stdin.read(), '<embedded>', 'exec')"],
+            input=body,
+            capture_output=True,
+            check=False,
+            text=True,
+        )
+        assert completed.returncode == 0, f"embedded_python_{index}: {completed.stderr}"
+
+
+def test_gcp_runtime_rejects_preexisting_symlink_before_mutation(tmp_path: Path) -> None:
+    script = (REPO_ROOT / "deploy" / "sync-gcp-leoclean-runtime.sh").read_text()
+    function_start = script.index("assert_existing_root_directory() {")
+    function_end = script.index("\n\nbackup_path() {", function_start)
+    trust_functions = script[function_start:function_end]
+    real_directory = tmp_path / "real-runtime"
+    real_directory.mkdir()
+    symlink = tmp_path / "runtime-link"
+    symlink.symlink_to(real_directory, target_is_directory=True)
+    harness = f"""
+set -euo pipefail
+sudo() {{
+  if [ "${{1:-}}" = -n ]; then
+    shift
+    if [ "${{1:-}}" = -u ]; then shift 2; fi
+  fi
+  "$@"
+}}
+{trust_functions}
+assert_existing_root_directory "$1"
+"""
+    completed = subprocess.run(
+        ["bash", "-s", "--", str(symlink)],
+        input=harness,
+        capture_output=True,
+        check=False,
+        text=True,
+    )
+
+    assert completed.returncode != 0
+
+
+def test_gcp_runtime_executable_configuration_override_gate() -> None:
+    script = (REPO_ROOT / "deploy" / "sync-gcp-leoclean-runtime.sh").read_text()
+    function_start = script.index("assert_unit_configuration() {")
+    function_end = script.index("\n\nassert_runtime_environment() {", function_start)
+    unit_configuration_function = script[function_start:function_end]
+    harness = f"""
+set -euo pipefail
+SERVICE=leoclean.service
+REMOTE_DROPIN_DIR=/etc/systemd/system/leoclean.service.d
+DROPIN_NAME=10-cloudsql-memory.conf
+systemctl() {{
+  case "$*" in
+    *--property=DropInPaths*) printf '%s\\n' "${{FAKE_DROPINS:-}}" ;;
+    *--property=EnvironmentFiles*) printf '%s\\n' "${{FAKE_ENVIRONMENT_FILES:-}}" ;;
+    *) return 90 ;;
+  esac
+}}
+{unit_configuration_function}
+assert_unit_configuration
+"""
+    reviewed = "/etc/systemd/system/leoclean.service.d/10-cloudsql-memory.conf"
+    cases = (
+        {
+            "FAKE_DROPINS": f"{reviewed} /etc/systemd/system/leoclean.service.d/99-conflict.conf",
+            "FAKE_ENVIRONMENT_FILES": "",
+        },
+        {"FAKE_DROPINS": reviewed, "FAKE_ENVIRONMENT_FILES": "/etc/leoclean-runtime.env"},
+    )
+    for environment in cases:
+        completed = subprocess.run(
+            ["bash", "-s"],
+            input=harness,
+            capture_output=True,
+            check=False,
+            env=environment,
+            text=True,
+        )
+        assert completed.returncode != 0
+
+    allowed = subprocess.run(
+        ["bash", "-s"],
+        input=harness,
+        capture_output=True,
+        check=False,
+        env={"FAKE_DROPINS": reviewed, "FAKE_ENVIRONMENT_FILES": ""},
+        text=True,
+    )
+    assert allowed.returncode == 0, allowed.stderr
+
+
+def test_gcp_runtime_absence_rollback_removes_every_created_directory(tmp_path: Path) -> None:
+    script = (REPO_ROOT / "deploy" / "sync-gcp-leoclean-runtime.sh").read_text()
+    function_start = script.index("backup_directory_state() {")
+    function_end = script.index("\nrestore_path() {", function_start)
+    directory_functions = script[function_start:function_end]
+    harness = f"""
+set -euo pipefail
+sudo() {{ "$@"; }}
+root="$1"
+backup_dir="$root/backup"
+mkdir -p "$backup_dir" "$root/usr/local" "$root/etc/systemd/system"
+runtime_grandparent="$root/usr/local/libexec"
+runtime_parent="$runtime_grandparent/livingip"
+runtime_bin="$runtime_parent/leoclean-kb"
+dropin_dir="$root/etc/systemd/system/service.d"
+{directory_functions}
+backup_directory_state "$runtime_grandparent" runtime_grandparent
+backup_directory_state "$runtime_parent" runtime_parent
+backup_directory_state "$runtime_bin" runtime_bin
+backup_directory_state "$dropin_dir" dropin_dir
+mkdir -p "$runtime_bin" "$dropin_dir"
+restore_directory_state "$runtime_bin" runtime_bin
+restore_directory_state "$runtime_parent" runtime_parent
+restore_directory_state "$runtime_grandparent" runtime_grandparent
+restore_directory_state "$dropin_dir" dropin_dir
+test ! -e "$runtime_grandparent"
+test ! -e "$dropin_dir"
+test -d "$root/usr/local"
+test -d "$root/etc/systemd/system"
+"""
+    completed = subprocess.run(
+        ["bash", "-s", "--", str(tmp_path)],
+        input=harness,
+        capture_output=True,
+        check=False,
+        text=True,
+    )
+
+    assert completed.returncode == 0, completed.stderr
+
+
+def test_gcp_runtime_rollback_never_reloads_or_restarts_after_validation_failure(tmp_path: Path) -> None:
+    script = (REPO_ROOT / "deploy" / "sync-gcp-leoclean-runtime.sh").read_text()
+    function_start = script.index("rollback_runtime() {")
+    function_end = script.index("\n\non_exit() {", function_start)
+    rollback_function = script[function_start:function_end]
+    action_log = tmp_path / "systemctl-actions"
+    harness = f"""
+set -u
+SERVICE=leoclean.service
+runtime_bin=/usr/local/libexec/livingip/leoclean-kb
+runtime_parent=/usr/local/libexec/livingip
+runtime_grandparent=/usr/local/libexec
+dropin_dir=/etc/systemd/system/leoclean.service.d
+DROPIN_NAME=10-cloudsql-memory.conf
+action_log="$1"
+sudo() {{
+  if [ "${{1:-}}" = systemctl ]; then
+    printf '%s\\n' "$2" >>"$action_log"
+    return 0
+  fi
+  "$@"
+}}
+restore_path() {{ return 0; }}
+restore_directory_state() {{ return 0; }}
+validate_restored_path() {{ [ "$2" != wrapper ]; }}
+validate_restored_directory() {{ return 0; }}
+assert_unit_configuration() {{ printf '%s\\n' unit-configuration >>"$action_log"; }}
+assert_service_running() {{ printf '%s\\n' assert-running >>"$action_log"; }}
+{rollback_function}
+rollback_runtime
+"""
+    completed = subprocess.run(
+        ["bash", "-s", "--", str(action_log)],
+        input=harness,
+        capture_output=True,
+        check=False,
+        text=True,
+    )
+
+    assert completed.returncode != 0
+    assert action_log.read_text(encoding="utf-8").splitlines() == ["stop"]