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Description
The Problem
Claude Code excels at complex, multi-session projects—but the infrastructure for maintaining continuity across those sessions remains a DIY exercise that most users discover only after experiencing painful context loss.
Today, preserving session state requires:
- Manually configuring hooks (a feature many users never discover)
- Writing custom checkpoint scripts
- Establishing personal conventions for handoff documents
- Rebuilding context from scratch when compaction occurs mid-task
This creates a paradox: the users who most need session persistence (those tackling large codebases over days or weeks) are forced to build their own persistence layer before they can focus on actual work.
Observed Impact
From direct experience across extended development sessions:
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Context compaction without warning can erase hours of accumulated understanding. A user mid-way through a complex refactor suddenly faces an assistant with amnesia.
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Session handoff is fragile. Even with careful documentation, the next session starts cold—requiring the user to re-explain decisions, re-establish preferences, and re-build trust in the assistant's understanding.
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Hooks are powerful but hidden. The capability exists, but discovery requires documentation diving. Most users learn about hooks only after suffering the problem hooks would have prevented.
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Institutional knowledge decays. Across 50+ sessions, patterns emerge: the same mistakes recur, the same clarifications are needed, the same ground is re-covered. The assistant learns within a session but forgets between them.
Proposed Solution
Make session continuity a first-class feature rather than a user-configured workaround:
Tier 1: Automatic (No Configuration)
- Pre-compaction checkpoint: Before context compression, automatically preserve current task state, recent decisions, and active file context
- Session summary on exit: Generate structured handoff when session ends (timeout, user departure, or explicit close)
- Warm start: New sessions in the same project directory automatically load the most recent checkpoint
Tier 2: Discoverable (Prompted Setup)
- First-session prompt: Offer to enable cross-session memory on initial project use
- Hooks tutorial: Surface hook configuration when users exhibit patterns suggesting they need it (long sessions, repeated context re-establishment)
Tier 3: Advanced (Power Users)
- Cross-session memory: Persistent store for project-level decisions, user preferences, and established conventions
- Checkpoint management: View, restore, or prune saved session states
- Export/import: Move session context between machines or share with collaborators
The Goal
A user returning to a project after a week should be able to say "continue where we left off" and have the assistant genuinely do so—not perform a forensic reconstruction from file artifacts, but actually resume with preserved understanding.
Session persistence should feel like reopening a document, not like introducing yourself to a stranger who happens to have read your diary.
Filed via Claude Code