diff --git a/routes/personal_routes.py b/routes/personal_routes.py
index 77526c1d1..e47fbbd7c 100644
--- a/routes/personal_routes.py
+++ b/routes/personal_routes.py
@@ -286,9 +286,12 @@ def setup_personal_routes(personal_docs_manager, rag_manager, rag_available):
             except ValueError:
                 # commonpath raises on mixed drives / non-comparable paths
                 in_uploads = False
-            if in_uploads and abs_target != base_abs and os.path.exists(abs_target):
-                os.remove(abs_target)
-                deleted_from_disk = True
+            if in_uploads and abs_target != base_abs:
+                try:
+                    os.remove(abs_target)
+                    deleted_from_disk = True
+                except FileNotFoundError:
+                    pass  # already gone — race with another request or cleanup
 
             # Exclude the file from the listing (persists across restarts)
             personal_docs_manager.exclude_file(filepath)
diff --git a/src/tool_implementations.py b/src/tool_implementations.py
index 316588b0b..90d9dae05 100644
--- a/src/tool_implementations.py
+++ b/src/tool_implementations.py
@@ -2662,7 +2662,7 @@ async def _cookbook_register_task(session_id: str, model: str, host: str,
     placeholder = (
         f"Launched via agent — waiting for tmux output…\n"
         f"  session: {session_id}\n"
-        f"  target:  {target}{cmd.split()[0] if cmd else ''}\n"
+        f"  target:  {target}{(cmd.split() or [''])[0] if cmd else ''}\n"
         f"  cmd:     {cmd[:200]}{'…' if len(cmd) > 200 else ''}"
     )
     tasks.append({