Preserving Context

Overview

Capture state proactively, not reactively. Before compaction or task switches, write down everything needed to resume seamlessly. If you wait until after compaction, the context is already gone.

What to Capture

| Category | Capture | |----------|---------| | Current work | Exact task, file path, progress (X of Y) | | Completed items | Which files changed and what was done | | Remaining items | What still needs doing, in order | | Pattern | The transformation being applied (so it continues consistently) | | Decisions | Key choices made and why (not just what) | | Blockers | Issues discovered, dependencies, failing tests | | Test state | Are tests passing? Which are failing and why? |

Checkpoint Template

Write this as a task description (via TaskUpdate) so it persists across compaction, and also communicate it to the user so they have it too:

## Checkpoint — [Task Name]

**Working on:** [specific task]
**Current file:** [path]
**Progress:** [X of Y complete]

### Completed
- [file1] — [what was done]
- [file2] — [what was done]

### Remaining
- [file3] — [what needs doing]
- [file4] — [what needs doing]

### Pattern Being Applied
[Describe the transformation so it can be continued consistently]

### Key Decisions
- [Decision]: [why this over alternatives]

### Blockers / Notes
- [Any issues or dependencies]

Good vs Bad Checkpoints

Bad: "Working on refactor. Some files done."

Good: "Renaming getUserById to fetchUserById across the codebase. Completed: src/services/user.ts, src/api/routes.ts, src/tests/user.test.ts. Remaining: src/middleware/auth.ts, src/utils/cache.ts. Pattern: find-and-replace function name + update all call sites + update test assertions. Tests currently failing on 2 import mismatches."

Red Flags — STOP and Checkpoint

| Thought | Action | |---------|--------| | "I'll remember where I was" | Write it down NOW | | "It's obvious what's next" | Obvious now ≠ obvious after compaction | | "Just one more thing then I'll document" | Checkpoint first, then continue | | "This is too small to checkpoint" | Small context loss compounds |

Integration with tracking-tasks

These two skills complement each other:

• tracking-tasks: Tracks WHAT tasks exist and their status
• preserving-context: Captures HOW to resume each task

Both should be used together before compaction.