Session restart loses all conversation context — memory system insufficient for continuation

Summary

When a user is advised to restart a Claude Code session (e.g. to fix a CLI issue), all in-session conversation context is lost. The persistent memory system does not capture enough state to allow the session to continue meaningfully.

Steps to reproduce

1. Have a multi-step development session with active work in progress (e.g. a feature branch with pending commits, a plan being executed).
2. Encounter any issue that prompts a session restart (e.g. CLI bug, ACLI issue).
3. Restart the session.
4. Ask Claude to "continue" — it has no memory of what was being done.

Expected behavior

Claude should either:

• Proactively persist a "continuation checkpoint" to its memory system before a session ends, summarizing the active task, next steps, and relevant context.
• OR the session restart should preserve enough context for Claude to resume without the user having to re-explain everything.

Actual behavior

Claude restarts with only what's in the git history and file diffs. All task-level context (what was being worked on, what decision was made, what step comes next) is lost. The user is forced to reconstruct context manually — an unfair burden especially when the restart was triggered by a tooling issue outside their control.

Impact

High frustration for users doing long-running architectural or development sessions. The recommendation to "restart the session" to fix a bug becomes a punishing action rather than a safe recovery.

Suggested fix

• Before any session ends (or when Claude detects it may be about to restart), auto-save a project memory entry: active task, last completed step, next pending step, open decisions.
• OR surface a /save-context slash command users can invoke before restarting.

Environment

• Claude Code CLI
• Model: claude-sonnet-4-6
• Branch context lost: feature/DEV-159876-mdc

🤖 Reported by Claude Code on behalf of user