jackwener/OpenCLI · error · CommandExecutionError

Failed to upload image to ChatGPT: ${err instanceof Error ?

Error message

Failed to upload image to ChatGPT: ${err instanceof Error ? err.message : String(err)}

What it means

uploadChatGPTImages threw inside the command, so it is wrapped into a CommandExecutionError prefixed 'Failed to upload image to ChatGPT: <underlying message>'. This is the exception path (as opposed to the {ok:false} path of error 627) — the upload helper itself raised, e.g. the attachment button/input was not found or a DOM interaction failed.

Source

Thrown at clis/chatgpt/image.js:109

        const preparedImages = imagePaths.length ? await prepareChatGPTImagePaths(imagePaths) : { ok: true, paths: [] };
        if (!preparedImages.ok) {
            throw new ArgumentError(preparedImages.reason);
        }

        // Navigate with full reload to clear React sidebar state before editing the draft.
        if (kwargs.project) {
            await navigateToProject(page, kwargs.project);
        } else {
            await page.goto(`https://${CHATGPT_DOMAIN}/new`, { settleMs: 2000 });
        }
        await clearChatGPTDraft(page);

        if (imagePaths.length) {
            let upload;
            try {
                upload = await uploadChatGPTImages(page, preparedImages.paths);
            } catch (err) {
                throw new CommandExecutionError(`Failed to upload image to ChatGPT: ${err instanceof Error ? err.message : String(err)}`);
            }
            if (!upload?.ok) throw new CommandExecutionError(upload?.reason || 'Failed to upload image to ChatGPT');
        }

        const beforeUrls = await getChatGPTVisibleImageUrls(page);

        // Send an explicit generation/editing prompt so ChatGPT returns image assets.
        const sent = await sendChatGPTMessage(page, buildPrompt(prompt, imagePaths.length));
        if (!sent) {
            throw new CommandExecutionError(
                'Failed to send image prompt to ChatGPT',
                `Open ${await currentChatGPTLink(page)} and verify the composer is ready.`,
            );
        }

        // ChatGPT briefly navigates to /c/{id} after sending, then may
        // redirect back to the home page. Poll until we capture the /c/ URL.
        let convUrl = '';

View on GitHub (pinned to 49907e53dc)

Solutions

Read the suffixed underlying message — it identifies the failing DOM step.
Retry the command; transient composer/hydration issues often clear on a second run.
Verify the composer is visible and usable in a browser session first.
Check file size/format against ChatGPT upload limits.
If it fails consistently, the upload selectors likely changed — update the library.

Example fix

// before
opencli chatgpt image "enhance" --image ./big-50mb.png   # upload throws mid-flight
// after
# resize/compress the image below ChatGPT limits, then
opencli chatgpt image "enhance" --image ./resized.png

Defensive patterns

Strategy: try-catch

Validate before calling

// Warm up the composer before uploading: navigate and confirm the page is interactive
await run('chatgpt image', prompt, '--image', path); // wrap with retry below

Type guard

null

Try / catch

async function uploadWithRetry(cmd, attempt = 0) {
  try {
    return await run('chatgpt image', cmd.prompt, '--image', cmd.image);
  } catch (err) {
    const msg = String(err.message);
    if (msg.includes('Failed to upload image to ChatGPT:') && attempt < 2) {
      await sleep(15_000 * (attempt + 1));
      return uploadWithRetry(cmd, attempt + 1);
    }
    throw err;
  }
}

Prevention

Retry transient upload failures with backoff
Keep image files under ChatGPT's size limits and in supported formats
Ensure the persistent browser session is healthy and freshly logged in
Check the wrapped underlying message — it names the failing step
Update the library if the upload control selectors drift after UI changes

When it happens

Trigger: `opencli chatgpt image "prompt" --image <path>` where uploadChatGPTImages(page, preparedImages.paths) throws — composer not rendered, attachment file input missing, page navigated mid-upload, or a Playwright/DOM error during the upload interaction.

Common situations: ChatGPT UI changed so the upload control selector is stale; page not fully hydrated when upload starts; file too large triggering a ChatGPT-side error that surfaces as an exception; transient network failure during upload; composer in an unexpected state (leftover draft or dialog).

Related errors

AI-assisted analysis of jackwener/OpenCLI@49907e53dc (2026-08-29). Data as JSON: /api/errors/701ef306543e80e3. Report an issue: GitHub.