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Named decision point for long-running tasks — PIVOT, REFINE, or PROCEED
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Based on SOC occupation classification
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Hook-based compaction suggestions at logical task boundaries
Context window management — track spend, decide when to compact, preserve state
Session-start orientation — loads context, surfaces learnings, confirms registry
Quality and semantic review — catches what automated tools miss
Planner → Architect → Critic deliberation loop — produces a formally validated ADR
| name | checkpoint |
| description | Named decision point for long-running tasks — PIVOT, REFINE, or PROCEED |
| version | 0.2.0 |
| level | 1 |
| triggers | ["checkpoint","check in","pivot or proceed","decision point","/checkpoint"] |
| context_files | ["context/learnings.md"] |
| steps | [{"name":"State Assessment","description":"What is done, in progress, and blocked?"},{"name":"Goal Alignment","description":"Does the current path still lead to the original goal?"},{"name":"Risk Surface","description":"What new risks or unknowns have appeared since the last checkpoint?"},{"name":"Decision","description":"PIVOT, REFINE, or PROCEED — with explicit rationale"},{"name":"Log if PIVOT","description":"If pivoting, write the abandoned approach and reason to context/learnings.md"}] |
A structured pause during long-running tasks. Prevents tunnel vision and catches drift before it compounds.
Without checkpoints, Claude continues executing a plan past the point where new information has invalidated one of its assumptions. The compound reliability math is real: at a 10% error rate per step, 10 steps yields 35% success. A checkpoint at step 5 resets the accumulation.
PROCEED — on track, no new risks, continue as planned.
REFINE — mostly correct, but one or two steps need adjustment. Document what changed and why, then continue.
PIVOT — the approach is fundamentally wrong or blocked. Stop. Re-plan the affected phase. Write the abandoned approach to learnings.md — this is high-value content.
A PIVOT is not a failure. A PIVOT without documentation is a failure.
Checkpoint — [task] — Step [N] of [N]
Completed: [list]
In Progress: [current step]
Blocked / New Info: [if any]
Decision: PROCEED / REFINE / PIVOT
Rationale: [one sentence]
Next: [specific next action]
Claude Code compacts at 93% of effective context (window minus 20k overhead). PSC checkpoints fire earlier:
| Level | Action |
|---|---|
| ~90% | Run checkpoint immediately — surface state, decide PIVOT/REFINE/PROCEED |
| ~95% | Blocking threshold — new tool calls may fail. Compact now. |
| Mid-debug | Do NOT compact — stack traces and error traces are the tool |
Signals that context is at 90%+: earlier parts of the conversation feel distant, rules from CLAUDE.md feel less active, you are uncertain about a constraint stated early in the session.
When in doubt, checkpoint. The cost of a false positive is one checkpoint. The cost of a missed threshold is silent context drift.
Do not issue a PROCEED when there are unresolved blockers. Acknowledge them and decide.
Do not PIVOT without writing the abandoned approach to learnings.md. Future sessions will revisit the same dead end without that record.