Image Upload Fails with "Invalid Response from the Jetpack Site"

[alinclamba]

Summary

A user is unable to upload images using the Jetpack app. They receive the error:

Failed to insert media. Tap to get more information.

Invalid response from the Jetpack site.

Here are two screenshots they shared from the mobile app:

Uploads work fine via WP Admin on a laptop (based on my tests), but waiting for user confirmation.

Details:

• Site: AT site with WordPress.com Business plan; check Slack or ZD for site URL
• Jetpack is fully connected (confirmed via Site Health & Jetpack Debug).
• Uploads work fine in WP Admin (tested by me, pending user confirmation).
• Device model: iPhone 13 Pro iOS 18.3.1 (user setup from the logs)
• Jetpack app version: 25.7.1

Findings So Far:

• Uploads via WP Admin (laptop) worked in my tests, but waiting for user confirmation.
• No images appear in the Media Library after the failed uploads.
• The site uses the Classic Editor, but since the Jetpack app doesn’t support it, the Block Editor is used in-app.=
• The user did not see a "Save Draft" option, which suggests the image was never uploaded at all.
• A past GH issue reported similar behavior, though it was closed as stale.

Next Steps & User Confirmation:

We’ve asked the user to confirm:

• If the issue occurs when uploading an image directly to the Media Library in the app (outside of posts/pages).
• If uploads work fine via WP Admin on a laptop (I tested this successfully, but waiting for their confirmation).

Logs provided by the user:

• They are shared in the ticket, not adding them here for privacy reasons.

User case:

• ZD ticket 9437650-zd-a8c
• Jetpack Debugger: Pc9OEs-v-p2 (🟩)
• Site URL: Pc9OEs-v-p2

[dangermattic]

Thanks for reporting! 👍

[alinclamba]

Per @dcalhoun suggestions in this Slack, I've based the user to try on a different WiFi and also from mobile data.
We're waiting for user response.

[dcalhoun]

We might also provide the user with a few files of varying sizes, to see if they are able to successfully upload smaller files. E.g., send them URLs of hosted image files of different sizes, ask them to download each, and attempt to upload each to their site.

[alinclamba]

Thanks David! I sent them three images.

[alinclamba]

Updates:

• I've sent three small images so they can test them
• Issue persists, they are still unable to upload images in the app

What would be the next step investigating this?