| "I updated TaskList, that's enough" | TaskList is step 1 of 4. /remember and /checkpoint-save persist across session boundaries; TaskList does not. |
| "Work is still in-flight, I'll run it at the end" | That's exactly when checkpoints matter — before a crash or context clear, not after. |
| "System-reminder already nudged me; I'll catch up later" | Nudges accumulate when skipped. Invoke the skill each boundary to prevent drift. |
| "Skipping one step won't matter" | /check-yourself IS the drift-preventer. Skipping once defeats its purpose. |
| "It's just a small edit, not a real boundary" | See the trigger enumeration above. If the event is listed, it is a boundary. |
| "§N parts 1 and 2 are sub-boundaries within §N" | The user pressed /proceed twice, which is two boundaries — not one. Your internal sectioning isn't the gate; the user's gesture is. |
| "Every /proceed doesn't need to spawn 4 sub-skills" | Yes, it does. The cost of running them each time is bounded (~30s + two file writes). The cost of skipping one is an unrecoverable context window if the session crashes between gates. That's the trade the skill was designed to make; don't re-litigate it mid-flow. |
| "I'm in flow, running remember+checkpoint-save is over-process" | Flow is when these matter most. You are most likely to crash, compact, or lose state exactly when reasoning has momentum. The skill is the brake that fires because you feel you don't need it. |
| "I'm in subagent-driven mode (/cat); inter-task /check-yourself is overkill" | The trigger enumeration says "a step in a multi-step plan is marked complete." The dispatch model does not change what counts as a step. If TaskUpdate flips status to completed, that IS the boundary — fire now, don't batch the catch-up to the next /pause. |
| "I dispatched N parallel subagents and treated their joint return as 1 boundary" | Each subagent return is a distinct boundary regardless of how the dispatches were timed. Parallel dispatch is a controller efficiency, not a boundary-merging operation. If 4 subagents return in one assistant turn, that is 4 boundaries — invoke /check-yourself between handling each return, or at minimum once before composing your single reply that addresses all of them. The "N returns / 1 turn" framing is the exact rationalization parallel dispatch invites; treat it as a red flag. |
| "I'm in a /listen-driven (or /cat / /super-cat / similar serial-enforcement) flow — the wrapper guarantees inner skills run, so the inner returns are sub-boundaries that collapse into the wrapper's single boundary" | /listen and /cat-family skills are serial enforcement, not boundary mergers. Each inner Skill-tool return is its own boundary regardless of what wraps the dispatch. If /listen drives 3 inner skill invocations, that's 3 returns and 3 /check-yourself opportunities — not 1 collapsed boundary at the wrapper close. The wrapper guarantees the inner skills RUN; it does not absorb their boundary semantics. |
| "I'm mid-TDD; red→green is one phase, not a boundary stack" | Wrong frame. Red failing run is one boundary (test-run completion). Green passing run is another. The SKILL.md file-write is a third. TDD momentum is the exact state the skill exists to interrupt — you feel efficient, so you skip the persistence that lets the session survive a crash. |
| "I verified inline with grep / git status" | Inline verification during a tool call is not /check-yourself. The skill is post-boundary reflection — surfacing drift you'd otherwise miss by forcing a pause, a task-list update, /remember, and /checkpoint-save. Pre-action verification does not trigger any of those writes. |
| "I'm in forward-motion between user asks — this is one continuous flow" | Forward motion is precisely when boundaries get skipped. User asks are separate gestures; the transcript is cut into discrete turns, and a discrete boundary between turns is discrete even when reasoning feels continuous. Invocation is the forcing function — without it, the "flow" state erases the boundaries you'd otherwise honor. If you notice yourself thinking "I'll batch the check-yourself after this next thing," you are already overdue by one. |