File deletion intermittently returns 500 before eventually succeeding

Deleting a file from a project intermittently fails with a 500 before a later retry succeeds. Observed repeatedly on 15-16 July in production.

Evidence

• One file returned 500 on four consecutive delete attempts, then succeeded.
• A second file returned 500 twice before succeeding.
• A third returned 500 twice the previous day.
• One delete returned 200, and an immediate repeat of the same request returned 404 — so the client cannot tell a real failure from an already-completed delete.

Why it matters

Deletion is a data-protection operation. A customer clearing their own content sees an error and cannot tell whether the data was removed. Repeated retries also mean the cleanup path runs more than once for the same file.

Suggested next step

Capture the underlying error behind the 500 (the response body is generic), make the delete idempotent so a repeat returns success rather than 404, and surface a clear outcome to the user.