[SYS-029] Claude Desktop: no compact/continue option when conversation hits context limit

Summary

When a Desktop conversation hits the context limit, Desktop shows a hard wall:

"This conversation is too long to continue. Start a new chat, or remove some tools to free up space."

There is no option, no autocompact, and no way to continue the session. The entire conversation is permanently lost for practical purposes.

Expected Behavior

Claude Desktop should offer the same context management options that CC CLI provides:

• command to summarize and continue
• behavior when context is running low
• Or at minimum: a warning before the limit is hit so the user can manually compact

Actual Behavior

Hard wall with no recovery. User must start a new chat and re-paste all context manually.

Impact

• Long-running Desktop sessions (PM agents, overnight analysis) are permanently killed when context limit hits
• Disproportionately impacts agentic workflows where sessions accumulate context over hours
• For a multi-hour overnight PM agent session, this is equivalent to a hard crash with no checkpoint
• CLI (CC) users have and — Desktop users have nothing

Reproduction

1. Start an agentic session in Claude Desktop
2. Run a long session (overnight agent, heavy tool use, etc.)
3. Observe: when context limit is reached, Desktop shows the hard wall message
4. No compact, no continue, no warning — session is dead

Environment

• Desktop 1.2581.0 (Windows 11 Pro x64)
• Also confirmed on 1.2278.0
• Persists after upgrade to latest Desktop version (tested 2026-04-15)

Related

• CC CLI has and that keep sessions alive — Desktop lacks both
• Related to Desktop renderer crashes (#44558) which also kill long sessions prematurely

Workaround

Use plain CLI window instead of Desktop for long-running agent sessions. and work in CLI.