claude-code - 💡(How to fix) Fix Session breaks after regressing a user message that contains an inline image [1 participants]

1. Session enters a bad state — user inputs don't get processed normally, or the next response is inconsistent with the regressed state (observed error framing: "Claude couldn't process that message. Try sending it again.")

TL;DR

Regressing a user message with an attached image in a long-running Claude Code session may leave the session in a broken state, requiring abandonment or forking to continue.

Guidance

• Verify that the issue is specific to messages with attached images by testing regress/retract on text-only messages to see if the session remains usable.
• Investigate the interaction between transcript size (1M context) and image attachment handling, as this may exacerbate the problem.
• Consider implementing a temporary workaround, such as avoiding regress/retract on messages with images or using a shorter context size, until a fix is available.
• Test the reproducibility of the issue with different types of image attachments (e.g., pasted vs. uploaded) to determine if the problem is specific to a particular attachment method.

Example

No code snippet is provided as the issue does not imply a specific code-related fix.

Notes

The issue may be related to how the Claude Code session handles image attachments and transcript history, particularly in long-running sessions with large context sizes. Further investigation is needed to determine the root cause and develop a permanent fix.

Recommendation

Apply workaround: Avoid using regress/retract on messages with images in long-running sessions until a fix is available, as this can help prevent the session from becoming broken and requiring abandonment or forking.