can1357/oh-my-pi · error

Gemini Files API upload initialization request failed

Error message

Gemini Files API upload initialization request failed

What it means

The initial 'start' resumable-upload POST to https://generativelanguage.googleapis.com/upload/v1beta/files threw (network-level failure), so the client discards the original cause and throws this generic message. This is a fetch-level failure — DNS, TLS, connection refused/reset, abort via request.signal — not an HTTP error status (that produces a different message).

Source

Thrown at packages/coding-agent/src/blob-broker/provider-files-gemini.ts:109

		async upload(request: ProviderFileUploadRequest): Promise<ProviderFileHandle> {
			const byteLength = request.bytes.byteLength;
			let startResponse: Response;
			try {
				startResponse = await fetchImpl(GEMINI_FILES_UPLOAD_URL, {
					method: "POST",
					headers: {
						"Content-Type": "application/json",
						"X-Goog-Upload-Command": "start",
						"X-Goog-Upload-Header-Content-Length": String(byteLength),
						"X-Goog-Upload-Header-Content-Type": request.mimeType,
						"X-Goog-Upload-Protocol": "resumable",
						"x-goog-api-key": credential,
					},
					body: JSON.stringify(request.filename ? { file: { display_name: request.filename } } : { file: {} }),
					signal: request.signal,
				});
			} catch {
				throw new Error("Gemini Files API upload initialization request failed");
			}
			if (!startResponse.ok) {
				throw new Error(`Gemini Files API upload initialization failed with HTTP ${startResponse.status}`);
			}

			const uploadUrl = startResponse.headers.get("X-Goog-Upload-URL")?.trim();
			if (!uploadUrl)
				throw new Error("Gemini Files API upload initialization response is missing X-Goog-Upload-URL");

			let finalizeResponse: Response;
			try {
				finalizeResponse = await fetchImpl(uploadUrl, {
					method: "POST",
					headers: {
						"Content-Length": String(byteLength),
						"X-Goog-Upload-Command": "upload, finalize",
						"X-Goog-Upload-Offset": "0",
					},

View on GitHub (pinned to 9690622007)

Solutions

1. Verify network connectivity to generativelanguage.googleapis.com (curl -v https://generativelanguage.googleapis.com).
2. Check whether the upload was cancelled — the request.signal you passed may have aborted (AbortError).
3. Check proxy/VPN/firewall settings; set HTTPS_PROXY if your network requires it.
4. Retry with backoff — transient connection resets are common for large uploads.
5. Note the original cause is swallowed; add a debug FetchImpl wrapper if you need the underlying error.

Example fix

// before: no diagnostics
await client.upload({ bytes, mimeType, signal });
// after: catch and retry with backoff on transient failures
try {
  return await client.upload({ bytes, mimeType, signal });
} catch (e) {
  if (String(e.message).includes("initialization request failed")) return retryWithBackoff(upload);
  throw e;
}

const reachable = await $`curl -sS -o /dev/null -w '%{http_code}' https://generativelanguage.googleapis.com/v1beta`.quiet().nothrow();
if (!reachable || reachable.text() === "000") throw new Error("No network path to Gemini API");

null

try {
  const handle = await client.upload(request);
} catch (error) {
  if (error instanceof Error && error.message.includes("initialization request failed")) {
    if (request.signal?.aborted) throw error; // cancelled by caller, do not retry
    return uploadWithBackoff(request);
  } else throw error;
}

When it happens

Trigger: fetchImpl() on the upload start request rejects: offline machine, DNS failure, TLS interception, connection reset, or request.signal aborted (AbortError).

Common situations: No internet / DNS misconfiguration; corporate proxy blocking generativelanguage.googleapis.com; firewall egress rules; request aborted by user cancel or timeout; IPv6 connectivity issues.

Related errors

• Gemini Files API upload finalization request failed
• AnthropicConnectionError
• OpenAI Files API upload request failed
• ${destination} upload failed with HTTP ${status}
• the upload response did not contain a valid direct URL

AI-assisted analysis of can1357/oh-my-pi@9690622007 (2026-08-31). Data as JSON: /api/errors/32da0df9cd6a3b9b. Report an issue: GitHub.