What causes "OpenAI Files API delete request failed" in can1357/oh-my-pi?

Confirm connectivity to api.openai.com (curl -X DELETE on the file URL with the key)

OpenAI Files API delete request failed

Error message

OpenAI Files API delete request failed

What it means

Thrown when the DELETE https://api.openai.com/v1/files/{id} request fails at the network level — fetch itself rejected (DNS, TLS, connection reset, abort). Like error 750, the original error is swallowed and replaced by this generic message; the API was never successfully reached.

Source

Thrown at packages/coding-agent/src/blob-broker/provider-files-openai.ts:138

					method: "DELETE",
					url: deleteUrl,
					headers: { Authorization: authorization },
				},
			};
		},
		async delete(handle: ProviderFileHandle): Promise<void> {
			if (handle.provider !== "openai" || typeof handle.id !== "string" || handle.id.trim().length === 0) {
				throw new Error("Cannot delete an invalid OpenAI file handle");
			}

			let response: Response;
			try {
				response = await request(`${OPENAI_FILES_URL}/${encodeURIComponent(handle.id)}`, {
					method: "DELETE",
					headers: { Authorization: authorization },
				});
			} catch {
				throw new Error("OpenAI Files API delete request failed");
			}
			if (!response.ok) {
				throw new Error(`OpenAI Files API delete failed with HTTP ${response.status}`);
			}
		},
	};
}

View on GitHub (pinned to 9690622007)

Solutions

Confirm connectivity to api.openai.com (curl -X DELETE on the file URL with the key)
Treat deletion as best-effort: catch, log, and retry later — leaked files can also be removed manually from the OpenAI dashboard
Check proxy/firewall rules allow DELETE requests to api.openai.com
Retry with backoff; deletions are idempotent (404 on retry is fine)

Example fix

// before: cleanup crashes on network blip
await client.delete(handle);
// after: best-effort deletion with retry
for (let attempt = 0; attempt < 3; attempt++) {
  try { await client.delete(handle); return; }
  catch (err) {
    if (!String(err.message).includes("delete request failed")) throw err;
    await Bun.sleep(2 ** attempt * 500);
  }
}
logger.warn("openai file delete deferred; will retry", { id: handle.id });

Defensive patterns

Strategy: retry

Type guard

function isDeleteNetworkFailure(err: unknown): boolean {
  return err instanceof Error && err.message === "OpenAI Files API delete request failed";
}

Try / catch

try {
  await client.delete(handle);
} catch (err) {
  if (isDeleteNetworkFailure(err)) {
    logger.warn("delete deferred (network); will retry", { id: handle.id });
    queueRetry(() => client.delete(handle)); // deletions are safe to retry
  } else throw err;
}

Prevention

Treat cleanup deletion as best-effort and queue retries
Remember deletes are idempotent — a later 404 just means success
Run cleanup jobs with connectivity checks / backoff
Collect failed deletions for periodic reconciliation against the dashboard

When it happens

Trigger: client.delete() where fetch throws: offline machine, DNS failure, proxy refusal, TLS interception, or an AbortSignal (none is passed here, so mainly network faults) during the DELETE.

Common situations: Cleanup runs after the network dropped; background deletion job executing during a VPN outage; corporate proxy blocking DELETE to api.openai.com.

Related errors

AI-assisted analysis of can1357/oh-my-pi@9690622007 (2026-08-31). Data as JSON: /api/errors/6de7dd14a66402fb. Report an issue: GitHub.