diff --git a/lib/merge.py b/lib/merge.py
index 1d54bf2..0e4ccef 100644
--- a/lib/merge.py
+++ b/lib/merge.py
@@ -308,7 +308,14 @@ async def _cherry_pick_onto_main(branch: str) -> tuple[bool, str]:
     rc, merge_base = await _git("merge-base", "origin/main", f"origin/{branch}")
     rc2, main_sha = await _git("rev-parse", "origin/main")
     if rc == 0 and rc2 == 0 and merge_base.strip() == main_sha.strip():
-        return True, "already up to date"
+        # Branch is descendant of main — but fork workflows (merge main into branch)
+        # create this state while still having new content. Check for actual diff.
+        rc_diff, diff_out = await _git(
+            "diff", "--stat", f"origin/main..origin/{branch}", timeout=10,
+        )
+        if rc_diff != 0 or not diff_out.strip():
+            return True, "already up to date"
+        logger.info("Branch %s is descendant of main but has new content — proceeding", branch)
 
     # Get extraction commits (oldest first), skip merge commits from fork workflows
     rc, commits_out = await _git(