[BUG] iOS - File/image upload fails with "failed to upload" error

[pchapman19]

App Version

2.5.2

Platform

• Android
• iOS

How you installed it

App Store

What happened?

Platform: iOS (iPhone)
Conduit version: [check the App Store for your version]
Open WebUI version: [check your instance - Admin > About]
Model: qwen3.5:9b

Describe the bug:
Attempting to upload an image via the file attachment button results in a
"failed to upload" error. The upload never completes.

To reproduce:

1. Start a new chat
2. Tap the attachment/file button
3. Select an image from the photo library
4. Observe "failed to upload" error

Expected behavior:
Image uploads successfully and is included in the message context.

Additional context:

• Self-hosted Open WebUI instance behind Caddy reverse proxy (HTTPS)
• Authentication via username/password
• Text chat, streaming, and all other features work correctly
• Image upload works fine via Safari on the same Open WebUI instance

What should have happened?

file upload

How to reproduce

Click + add file or photo

Does this happen every time?

Yes, every time

When did this start?

Every time

Screenshots

Logs

No response

[cogwheel0]

can you check your openwebui logs for an error?

[pchapman19]

Yes. Checked logs. Resolved with server-side config fix. Root cause was missing image extensions (jpg, jpeg, png) in Open WebUI's allowed file extensions list (Admin Panel > Documents). Once added, uploads work reliably. Conduit does send some requests with incorrect MIME type (application/x-x509-ca-cert) per upload attempt, but the correct image/jpeg request also comes through and succeeds. Net result: functional. The MIME type issue is a latent bug but not user-visible once the server config is correct. Thanks