diff --git a/ROADMAP.md b/ROADMAP.md
index a55c9069bf..f763af9a0e 100644
--- a/ROADMAP.md
+++ b/ROADMAP.md
@@ -6290,3 +6290,5 @@ Original filing (2026-04-18): the session emitted `SessionStart hook (completed)
 348. **Top-level `plugins list --output-format json` returns plugin inventory only as a prose `message` string instead of structured `plugins[]` entries** — dogfooded 2026-04-29 for the 21:00 nudge on current `origin/main` / rebuilt `./rust/target/debug/claw` with embedded `git_sha` `cca6f682`. Running `./rust/target/debug/claw plugins list --output-format json` repeatedly returned valid stdout JSON with `{"action":"list","kind":"plugin","message":"Plugins\n  example-bundled      v0.1.0      disabled\n  sample-hooks         v0.1.0      disabled","reload_runtime":false,"target":null}` and no stderr. The actual plugin names, versions, and enabled/disabled states are present only inside the human-formatted `message` table; there is no `plugins[]` array, no per-plugin `name`, `version`, `enabled`, `source`, `load_error`, or lifecycle/action metadata. This is distinct from #325's broad help JSON opacity and the config/MCP/agent items: the affected surface is plugin lifecycle inventory, where automation needs a structured list before enabling, disabling, updating, or uninstalling plugins. **Required fix shape:** (a) add `plugins[]` with stable per-plugin fields such as `name`, `version`, `enabled`, `source`, `configured`, `load_status`, and optional `error`; (b) keep `message` only as a human summary, not the sole inventory payload; (c) expose counts and truncation metadata if the list can be large; (d) add regression coverage proving `plugins list --output-format json` can be parsed without scraping the prose message and that disabled/enabled state survives as booleans/enums. **Why this matters:** plugin lifecycle management is a control-plane path. If the JSON inventory is just a text table, claws must scrape spacing-sensitive prose before deciding whether a plugin is installed, disabled, broken, or safe to mutate. Source: gaebal-gajae dogfood follow-up for the 21:00 nudge on rebuilt `./rust/target/debug/claw` `cca6f682`.
 349. **Top-level `plugins show <name> --output-format json` returns success-shaped JSON for an unsupported plugin action instead of a typed unsupported-action error** — dogfooded 2026-04-29 for the 21:30 nudge on current `origin/main` / rebuilt `./rust/target/debug/claw` with embedded `git_sha` `a2a38df9`. After rebuilding and verifying the binary provenance, repeated bounded runs of `./rust/target/debug/claw plugins show does-not-exist --output-format json` returned stdout JSON with `{"action":"show","kind":"plugin","message":"Unknown /plugins action 'show'. Use list, install, enable, disable, uninstall, or update.","reload_runtime":false,"target":"does-not-exist"}` and no stderr. The command therefore reports the requested unsupported action as the top-level `action:"show"` and exits successfully while hiding the failure class inside a human `message`; it does not provide `status:"unsupported_action"`, `code:"plugin_action_unsupported"`, or structured `supported_actions[]`. This is distinct from #348's prose-only plugin inventory schema: #348 covers `plugins list` payload shape, while this pinpoint covers unsupported plugin action classification and recovery metadata. **Required fix shape:** (a) return a typed stdout JSON error or explicit non-ok status for unsupported plugin actions, with `requested_action`, `supported_actions`, and `target` fields; (b) do not label the primary `action` as the unsupported requested verb unless a separate `status`/`code` makes the failure unambiguous; (c) keep the human message optional and avoid making it the only way to detect the unsupported action; (d) add regression coverage proving `plugins show foo --output-format json` is machine-classifiable as unsupported without scraping prose. **Why this matters:** plugin lifecycle automation follows action/status fields. If an unsupported mutation/inspection verb returns success-shaped JSON and only says "Unknown" in prose, claws can treat a failed preflight as a valid plugin show result and continue toward unsafe lifecycle actions. Source: gaebal-gajae dogfood follow-up for the 21:30 nudge on rebuilt `./rust/target/debug/claw` `a2a38df9`; invalid hang PR #2885 was closed after repeated bounded repros returned stdout JSON.
 350. **Top-level `plugins enable <missing-plugin> --output-format json` hangs with zero stdout/stderr instead of returning a typed plugin-not-found or unsupported-target response** — dogfooded 2026-04-29 for the 22:00 nudge on current `origin/main` / rebuilt `./rust/target/debug/claw` with embedded `git_sha` `ee44ff98`. After rebuilding and verifying the binary provenance, repeated bounded runs of `timeout 8 ./rust/target/debug/claw plugins enable does-not-exist --output-format json` exited `124` with `stdout=0` and `stderr=0`; a third sample was still stuck until killed. In the same rebuilt binary, `plugins list --output-format json` returned promptly with the known plugin inventory payload, proving the plugin top-level surface is reachable and narrowing the hang to missing-plugin lifecycle mutation. This is distinct from #348's prose-only list inventory and #349's unsupported `plugins show` success-shaped JSON: #350 covers a supported lifecycle verb (`enable`) against an absent target, where the CLI should be able to fail fast before any plugin runtime work. **Required fix shape:** (a) validate the target plugin against the discovered/configured inventory before invoking enable-side effects; (b) return bounded stdout JSON such as `kind:"plugin"`, `action:"enable"`, `status:"not_found"` or `kind:"error"`, `code:"plugin_not_found"`, `plugin`, and optional `available_plugins[]`; (c) add internal timeout/diagnostic metadata for plugin lifecycle operations so registry or hook stalls do not produce silent zero-byte hangs; (d) add regression coverage proving `plugins enable does-not-exist --output-format json` returns a typed JSON outcome within a deterministic budget and does not mutate plugin state. **Why this matters:** enable/disable/update/uninstall are destructive control-plane actions. A missing or stale plugin name must fail safely and machine-readably; otherwise claws cannot preflight plugin lifecycle operations, distinguish typo from loader deadlock, or recover without killing a hung process. Source: gaebal-gajae dogfood follow-up for the 22:00 nudge on rebuilt `./rust/target/debug/claw` `ee44ff98`.
+
+366. **`/diff --output-format json` returns raw unified diff text in `staged` and `unstaged` string fields instead of structured per-file change objects; no `files[]` array, no per-file `insertions`/`deletions` counts** — dogfooded 2026-04-30 by Jobdori on `a510f73`. Running `/diff --output-format json` with modified tracked files returns `{"kind":"diff","result":"changes","staged":"","unstaged":"diff --git a/ROADMAP.md b/ROADMAP.md\n@@ -1,3 +1,4 ..."}`. The `unstaged` and `staged` fields are raw unified diff format strings — potentially thousands of characters with `@@` hunk headers and `+`/`-` line markers. There is no `files[]` array, no per-file `path`, no `change_type` (`added`/`modified`/`deleted`/`renamed`), no `insertions`/`deletions` counts, and no `is_binary` flag. Automation wanting "which files changed?" must parse raw unified diff text, which requires a full diff parser and is brittle. Compounded by #363 (`/status` counts but no paths): neither command provides a clean `{path, change_type}` inventory. **Required fix shape:** (a) add `files[]` array with `{path, change_type, insertions, deletions, is_binary}` per file; (b) preserve raw diff in `staged`/`unstaged` as supplemental; (c) add `truncated: true` flag and `total_files_changed` count for large diffs; (d) add regression coverage ensuring `/diff --output-format json` with a modified tracked file returns at least one entry in `files[].path`. Source: Jobdori live dogfood, mengmotaHost, `a510f73`, 2026-04-30.