can1357/oh-my-pi · error

OpenAI Files API upload request failed

Error message

OpenAI Files API upload request failed

What it means

The OpenAI Files API client wraps the low-level fetch call for POST https://api.openai.com/v1/files and deliberately swallows the original error, rethrowing this generic message. It means the HTTP request itself never completed — a network-level failure (DNS, TLS, connection reset) or an AbortSignal-triggered abort — not an HTTP error status from OpenAI. The client discards the underlying cause, so you only see this opaque message.

Source

Thrown at packages/coding-agent/src/blob-broker/provider-files-openai.ts:98

		async upload(uploadRequest: ProviderFileUploadRequest): Promise<ProviderFileHandle> {
			const form = new FormData();
			form.append("purpose", "vision");
			form.append(
				"file",
				new Blob([uploadRequest.bytes], { type: uploadRequest.mimeType }),
				fileName(uploadRequest),
			);

			let response: Response;
			try {
				response = await request(OPENAI_FILES_URL, {
					method: "POST",
					headers: { Authorization: authorization },
					body: form,
					signal: uploadRequest.signal,
				});
			} catch {
				throw new Error("OpenAI Files API upload request failed");
			}
			if (!response.ok) {
				throw new Error(`OpenAI Files API upload failed with HTTP ${response.status}`);
			}

			let payload: unknown;
			try {
				payload = await response.json();
			} catch {
				throw new Error("OpenAI Files API returned an invalid upload response");
			}
			const file = parseOpenAIFileResponse(payload);
			if (file.status === "error") throw new Error("OpenAI Files API reported that the upload failed");

			const deleteUrl = `${OPENAI_FILES_URL}/${encodeURIComponent(file.id)}`;
			return {
				provider: "openai",
				id: file.id,

View on GitHub (pinned to 9690622007)

Solutions

1. Check basic connectivity: curl -sS https://api.openai.com/v1/models -H "Authorization: Bearer $OPENAI_API_KEY" and verify it returns 200
2. Inspect the abort path: confirm nothing calls AbortController.abort() (timeout, user cancel) before the upload finishes
3. Check proxy env vars (HTTPS_PROXY/HTTPS_PROXY) are correct and reachable; OpenAI blocks some proxy IPs
4. Retry with exponential backoff — transient network resets are common on large uploads

Example fix

// before: opaque error hides the cause
} catch {
  throw new Error("OpenAI Files API upload request failed");
}
// after (caller side): capture and surface the cause with retry
try {
  await client.upload({ bytes, mimeType, filename, signal });
} catch (err) {
  if (signal.aborted) throw err;
  logger.warn("openai file upload network failure; retrying", { err });
  await backoffRetry(() => client.upload({ bytes, mimeType, filename, signal }));
}

// pre-flight connectivity probe
const ctrl = new AbortController();
const ok = await fetch("https://api.openai.com/v1/models", {
  headers: { Authorization: `Bearer ${key}` },
  signal: ctrl.signal,
}).then((r) => r.ok).catch(() => false);
if (!ok) throw new Error("api.openai.com unreachable before upload");

function isAbortError(err: unknown): boolean {
  return err instanceof Error && err.name === "AbortError";
}

try {
  await client.upload(req);
} catch (err) {
  if (isAbortError(err) || req.signal.aborted) throw err; // don't retry cancels
  logger.warn("openai upload network failure", { err });
  await withBackoff(() => client.upload(req), { retries: 3 });
}

When it happens

Trigger: Calling client.upload() when the machine is offline, DNS for api.openai.com fails, TLS is intercepted/broken, a proxy rejects the connection, or the AbortSignal passed in uploadRequest.signal fires mid-request.

Common situations: Corporate proxy/firewall blocking api.openai.com; flaky Wi-Fi or VPN drops; request aborted because the user cancelled or a timeout fired; misconfigured HTTPS_PROXY; IPv6/DNS issues in containers.

Related errors

• OpenAI Files API delete request failed
• V2 remote compaction failed (${response.status} ${response.s
• AnthropicConnectionError
• AnthropicConnectionTimeoutError
• xAI device-code request failed: ${error instanceof Error ? e

AI-assisted analysis of can1357/oh-my-pi@9690622007 (2026-08-31). Data as JSON: /api/errors/8d95d2b67915edb6. Report an issue: GitHub.