diff --git a/cheddahbot/tools/press_release.py b/cheddahbot/tools/press_release.py
index 64b19e5..061d649 100644
--- a/cheddahbot/tools/press_release.py
+++ b/cheddahbot/tools/press_release.py
@@ -684,18 +684,27 @@ def write_press_releases(
 
     # ── ClickUp: upload docx attachments + comment ─────────────────────
     uploaded_count = 0
+    failed_uploads: list[str] = []
     if clickup_task_id and cu_client:
         try:
             for path in docx_files:
                 if cu_client.upload_attachment(clickup_task_id, path):
                     uploaded_count += 1
                 else:
+                    failed_uploads.append(path)
                     log.warning("ClickUp: failed to upload %s for task %s", path, clickup_task_id)
+            upload_warning = ""
+            if failed_uploads:
+                paths_list = "\n".join(f"  - {p}" for p in failed_uploads)
+                upload_warning = (
+                    f"\n⚠️ Warning: {len(failed_uploads)} attachment(s) failed to upload. "
+                    f"Files saved locally at:\n{paths_list}"
+                )
             cu_client.add_comment(
                 clickup_task_id,
                 f"📎 Saved {len(docx_files)} press release(s). "
                 f"{uploaded_count} file(s) attached.\n"
-                f"Generating JSON-LD schemas next...",
+                f"Generating JSON-LD schemas next...{upload_warning}",
             )
             log.info(
                 "ClickUp: uploaded %d attachments for task %s", uploaded_count, clickup_task_id