diff --git a/src/runtime/SSHRuntime.ts b/src/runtime/SSHRuntime.ts
index 37cb22cf2..af94e0ace 100644
--- a/src/runtime/SSHRuntime.ts
+++ b/src/runtime/SSHRuntime.ts
@@ -985,9 +985,33 @@ export class SSHRuntime implements Runtime {
             cd ${shescape.quote(deletedPath)} || exit 1
             git diff --quiet --exit-code && git diff --quiet --cached --exit-code || exit 1
             if git remote | grep -q .; then
+              # First, check the original condition: any commits not in any remote
               unpushed=$(git log --branches --not --remotes --oneline)
               if [ -n "$unpushed" ]; then
-                echo "$unpushed" | head -10 >&2
+                # Get current branch for better error messaging
+                BRANCH=$(git rev-parse --abbrev-ref HEAD 2>/dev/null)
+                
+                # Get default branch (try origin/HEAD, fallback to main, then master)
+                DEFAULT=$(git symbolic-ref refs/remotes/origin/HEAD 2>/dev/null | sed 's@^refs/remotes/origin/@@')
+                if [ -z "$DEFAULT" ]; then
+                  if git rev-parse --verify origin/main >/dev/null 2>&1; then
+                    DEFAULT="main"
+                  elif git rev-parse --verify origin/master >/dev/null 2>&1; then
+                    DEFAULT="master"
+                  fi
+                fi
+                
+                # If we have both branch and default, use show-branch for better output
+                if [ -n "$BRANCH" ] && [ -n "$DEFAULT" ] && git show-branch "$BRANCH" "origin/$DEFAULT" >/dev/null 2>&1; then
+                  echo "Branch status compared to origin/$DEFAULT:" >&2
+                  echo "" >&2
+                  git show-branch "$BRANCH" "origin/$DEFAULT" 2>&1 | head -20 >&2
+                  echo "" >&2
+                  echo "Note: If your PR was squash-merged, these commits are already in origin/$DEFAULT and safe to delete." >&2
+                else
+                  # Fallback to just showing the commit list
+                  echo "$unpushed" | head -10 >&2
+                fi
                 exit 2
               fi
             fi