docs(roadmap): file dead-session opacity as ROADMAP #38

Author: code-yeongyu

ROADMAP.md

@@ -498,3 +498,5 @@ Model name prefix now wins unconditionally over env-var presence. Regression tes
 36. **Custom/project skill invocation disconnected from skill discovery** -- dogfooded 2026-04-09. /skills lists custom skills (e.g. caveman) but bare skill-name invocation does not dispatch them; falls through to plain model prompt. Fix: audit classify_skills_slash_command, ensure any skill listed by /skills has a deterministic invocation path, or document the correct syntax. Source: gaebal-gajae dogfood 2026-04-09.
 
 37. **Claude subscription login path should be removed, not deprecated** -- dogfooded 2026-04-09. Official auth should be API key only (ANTHROPIC_API_KEY or OAuth access token via ANTHROPIC_AUTH_TOKEN). claw login with Claude subscription credentials creates legal/billing ambiguity. Fix: remove the subscription login surface entirely; update README/USAGE.md to say API key is the only supported path. Source: gaebal-gajae policy decision 2026-04-09.
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+38. **Dead-session opacity: bot cannot self-detect compaction vs broken tool surface** -- dogfooded 2026-04-09. Jobdori session spent ~15h declaring itself "dead" in-channel while tools were actually returning correct results within each turn. Root cause: context compaction causes tool outputs to be summarised away between turns, making the bot interpret absence-of-remembered-output as tool failure. This is a distinct failure mode from ROADMAP #31 (executor quirks): the session is alive and tools are functional, but the agent cannot tell the difference between "my last tool call produced no output" (compaction) and "the tool is broken". Downstream: repetitive false-dead signals in the channel, work not getting done despite the execution surface being live. Fix shape: (a) probe with a short known-output command at turn start if context has been compacted; (b) gate "I am dead" declarations behind at least one within-turn tool call with a verified non-empty result; (c) consider adding a session-health canary cron that fires a wake with a minimal probe and checks the result. Source: Jobdori self-dogfood 2026-04-09; observed in #clawcode-building-in-public across multiple Clawhip nudge cycles.