[Bugs] Once this error appears:

**Mood:** 😔
**Category:** Bugs

Once this error appears:

Error: Execution failed: Error: Failed to get response from the AI model; retried 5 times (total retry wait time: 6.34 seconds) Last error: Error: The attached image or document is too large to send natively through CAPI Responses. Try a smaller attachment or fewer attachments. (9.1 MB request; 5.0 MB limit)

There seem no way to recover the session. It get stuck in this keep repeating the failure error ...

---
| Field | Value |
| --- | --- |
| App version | 0.2.24 |
| OS | macOS 26.5.0 |
| Theme | GitHub |
| Path | /chat |
| Tenure | Week 2 |

Start by reproducing the failure from the /chat path with an attachment larger than the stated limit, then trace how repeated request errors affect the session. Done means the error no longer traps the session in a repeating failure and the user has a way to recover or continue.

Written by the indexing model from the issue text.