Working-state continuity: survive compaction and /clear (the long-session "goes dumb" problem)

Summary

Working state doesn't survive context compaction or /clear. On long sessions the assistant slowly "goes dumb" — re-deriving things, forgetting in-flight threads, repeating work — and after a /clear it has no idea where we just were. The forgetting and the resulting confident-but-wrong guessing are the same problem. I've built a hook-layer workaround that fixes it, and I think the pattern belongs in the product.

The problem (two failure modes, both chronic)

1. Long-session degradation. As context fills and auto-compaction summarizes, granular working state gets compressed away — which file is mid-edit, what was just deployed-but-not-committed, the exact next action. The assistant quietly re-derives, forgets in-flight threads, and repeats work. You usually don't notice until it's already lost.
2. Cold-start amnesia after /clear or compaction. A fresh session reloads CLAUDE.md but has no sense of where we just were. The user spends real effort re-orienting ("where are we, why aren't we moving forward?"). That handoff across the clear boundary is the single weakest link.

The hidden cost isn't just time — when the model loses real state it guesses to fill the gap, which is exactly how you get hallucinated/invented state.

Why existing tools don't close it

• CLAUDE.md / project memory — great for static facts; wrong home for dynamic working state, and nothing keeps it short or current.
• Auto-compaction summary — a narrative recap, not a structured/actionable current focus / last action / next action / live state object.
• No working-state object survives BOTH compaction and /clear as a distinct, always-first, model-maintained scratchpad.

What I built as a workaround (maps directly onto features you could ship)

1. Pinned "RIGHT NOW" block at the top of the auto-loaded memory index (~5 lines: current focus, last action, next action, live state — branch/URLs/IDs). First thing in context every session.
2. PreCompact hook that snapshots working state the instant before compaction — leads with the RIGHT NOW block (pulled live from memory), then appends tracked-only git status so deployed-but-uncommitted work can't be silently lost. Also increments a compaction counter.
3. SessionStart hook that re-injects that snapshot, but only if recent (≤2h), so a stale file doesn't pollute a genuinely fresh start.
4. Watchdog (UserPromptSubmit hook) that reads the compaction counter + elapsed time and proactively nudges a checkpoint-and-/clear before degradation gets bad.
5. Wrap discipline that rewrites the RIGHT NOW block at session end.

It works — but no user should have to hand-roll PowerShell hooks and a memory taxonomy to keep their agent from going senile mid-task.

Concrete feature requests

• [ ] A first-class "working scratchpad" — short, structured, model-maintained (current focus, next action, live artifacts), always re-injected first, updated automatically, and guaranteed to survive both compaction and /clear, kept distinct from the conversation summary.
• [ ] Automatic pre-compaction capture of that scratchpad + uncommitted/deployed working state (built-in, not a user hook).
• [ ] Surface compaction to the user with a one-click "checkpoint & restart" flow, instead of silent degradation noticed only once the assistant is already lost.
• [ ] A guaranteed pinned-top region in CLAUDE.md/memory that's always first in context.

Before/after

Before: a mid-session compaction left the assistant having forgotten I'd just deployed a Lambda but not committed it — so it either redid the work or assumed it was committed and moved on, leaving real drift between deployed and source. After: the first thing in the new context is "you deployed X, it's uncommitted, commit it" + the exact next action. A relearn-for-an-hour event became a two-line handoff.

Happy to share the full hook scripts and memory layout if useful.

(Filed by a daily heavy user; also sent via email to the feedback address. Cross-posting here because this is where the product team actually lives.)