Context compaction disrupts workflow mid-task, no user feedback mechanism

Problem

During active development sessions, context compaction triggers abruptly — often mid-task — forcing the user to restart or lose conversational flow. There is no warning, no progress indicator, and no way to recover the prior context gracefully.

For paying customers on the Max plan ($200/month), this is a significant pain point. The experience feels like the tool is working against you at the moment you need it most — deep in a multi-file refactor or iterative UI work.

Specific experience

• Working on a multi-file UI styling task (3-4 files, iterative changes with screenshot feedback)
• After approximately 1 minute of active back-and-forth, hit "Context limit reached" with the only options being /compact or /clear
• Compaction loses the nuanced conversational state (what was tried, what feedback was given, what remains to be done)
• The user had to re-explain their intent after compaction, duplicating effort

What would help

1. Proactive warning — alert the user when context is approaching the limit, so they can choose to compact at a natural breakpoint rather than being interrupted mid-thought
2. Better compaction fidelity — preserve more of the task-specific context (which files were being edited, what changes were requested, what feedback was given) rather than just a generic summary
3. Transparency — show users how much context budget remains (even a simple percentage or progress bar) so they can plan their workflow accordingly
4. Acknowledgement — some form of feedback loop so paying customers know their concerns about this are being heard and prioritised

Environment

• Claude Code CLI (Max plan, $200/month)
• Claude Opus 4.6
• macOS