diff --git a/ROADMAP.md b/ROADMAP.md
index ca63e333ab..66ad62ba6e 100644
--- a/ROADMAP.md
+++ b/ROADMAP.md
@@ -6300,3 +6300,5 @@ Original filing (2026-04-18): the session emitted `SessionStart hook (completed)
 358. **Top-level `cost --help --output-format json` hangs with zero stdout/stderr instead of returning bounded command help JSON** — dogfooded 2026-04-30 for the 02:00 nudge on current `origin/main` / rebuilt `./rust/target/debug/claw` with embedded `git_sha` `d95b230c`. After rebuilding and verifying the binary provenance, repeated bounded runs of `timeout 8 ./rust/target/debug/claw cost --help --output-format json` exited `124` with `stdout=0` and `stderr=0`. In the same rebuilt binary, `version --output-format json` returned promptly with version/build metadata, proving the binary itself and the JSON output path are reachable; the hang is specific to the cost help path, though other help surfaces have separate known JSON contract issues (#356/#357). **Required fix shape:** (a) make `cost --help --output-format json` return static/bounded stdout JSON with `kind:"help"` or `kind:"cost"`, `action:"help"`, usage, options, examples, supported output formats, and related slash/direct commands; (b) ensure help rendering does not initialize slow cost/session/accounting providers; (c) if any dynamic provider is accidentally consulted, return a typed JSON timeout/unavailable error instead of hanging; (d) add regression coverage proving cost help in JSON mode returns within a deterministic budget. **Why this matters:** cost/tokens surfaces are commonly consumed by automation for budgeting. If even cost help can hang silently, claws cannot discover cost command semantics or present safe budget diagnostics before running potentially slow accounting paths. Source: gaebal-gajae dogfood follow-up for the 02:00 nudge on rebuilt `./rust/target/debug/claw` `d95b230c`.
 380. **Top-level `tokens --help --output-format json` hangs with zero stdout/stderr instead of returning bounded command help JSON** — dogfooded 2026-04-30 for the 02:30 nudge on current `origin/main` / rebuilt `./rust/target/debug/claw` with embedded `git_sha` `d95b230c`. After verifying #358 covered `cost --help`, a fresh adjacent probe on the token-budget surface showed the same silent failure class: repeated bounded runs of `timeout 8 ./rust/target/debug/claw tokens --help --output-format json` exited `124` with `stdout=0` and `stderr=0`. In the same rebuilt binary, `version --output-format json` returned promptly with version/build metadata, proving the binary itself and JSON output path are reachable. This is distinct from #358's cost help hang: the affected surface is the sibling `tokens` command help, which agents use before estimating prompt/session token budgets. **Required fix shape:** (a) make `tokens --help --output-format json` return static/bounded stdout JSON with `kind:"help"` or `kind:"tokens"`, `action:"help"`, usage, options, examples, supported output formats, and related slash/direct commands; (b) ensure help rendering does not initialize slow token accounting, session, or provider state; (c) if any dynamic provider is consulted, return a typed JSON timeout/unavailable error instead of hanging; (d) add regression coverage proving tokens help in JSON mode returns within a deterministic budget. **Why this matters:** token budgeting is a preflight clawability surface. If help hangs silently, automation cannot safely discover how to inspect or constrain token usage before running expensive prompts, and budget-aware wrappers stall at the discovery step. Source: gaebal-gajae dogfood follow-up for the 02:30 nudge on rebuilt `./rust/target/debug/claw` `d95b230c`.
 381. **Top-level `cache --help --output-format json` hangs with zero stdout/stderr instead of returning bounded command help JSON** — dogfooded 2026-04-30 for the 03:00 nudge on current `origin/main` / rebuilt `./rust/target/debug/claw` with embedded `git_sha` `d95b230c`. After #358 and #380 landed for the cost/tokens preflight help hangs, a fresh adjacent probe on the cache-control surface showed the same silent failure class: repeated bounded runs of `timeout --kill-after=1s 8s ./rust/target/debug/claw cache --help --output-format json` exited `124` with `stdout=0` and `stderr=0`. In the same rebuilt binary, `version --output-format json` returned promptly with version/build metadata, proving the binary itself and JSON output path are reachable. This is distinct from the separate `/cache` slash-command envelope mismatch class: the affected surface here is top-level `cache` command help, where agents need bounded local discovery before deciding whether to inspect, clear, or summarize cache state. **Required fix shape:** (a) make `cache --help --output-format json` return static/bounded stdout JSON with `kind:"help"` or `kind:"cache"`, `action:"help"`, usage, options, examples, supported output formats, and related slash/direct commands; (b) ensure help rendering does not initialize slow cache/session/provider state; (c) if any dynamic provider is consulted, return a typed JSON timeout/unavailable error instead of hanging; (d) add regression coverage proving cache help in JSON mode returns within a deterministic budget. **Why this matters:** cache inspection and cleanup are recovery/control-plane operations. If cache help hangs silently, claws cannot safely discover cache semantics before attempting cleanup, and automation stalls before it can choose a non-destructive cache action. Source: gaebal-gajae dogfood follow-up for the 03:00 nudge on rebuilt `./rust/target/debug/claw` `d95b230c`.
+
+423. **`diff --output-format json` returns `staged` and `unstaged` as raw `git diff` prose strings, not structured file-change objects — automation must parse the diff text to identify which files changed** — dogfooded 2026-05-01 by Jobdori on `e939777f`. Running `claw diff --output-format json` in a repo with unstaged changes returns `{"kind":"diff","result":"changes","staged":"","unstaged":"diff --git a/ROADMAP.md b/ROADMAP.md\nindex ca63e33..2e4b74e 100644\n--- a/ROADMAP.md\n+++ b/ROADMAP.md\n@@ -1,3 +1,4 @@\n+// test change\n ..."}`. The `staged` and `unstaged` fields are raw multi-line `git diff` output strings. A claw that wants to know which files changed, how many lines were added/removed, or whether a specific path is in the diff must parse the raw unified diff format — there are no structured `files:[{path, additions, deletions, status}]` fields, no `changed_files_count`, no per-file change summary. The `result` field (`"changes"`, `"clean"`, `"no_git_repo"`) is machine-readable, but everything else is raw prose. Automation that relies on `diff --output-format json` to make decisions (e.g. "did the test files change?", "are there staged changes before a commit?") must implement a full unified diff parser. **Required fix shape:** (a) add a `files` field containing structured per-file change metadata: `{path, status:"added"|"modified"|"deleted"|"renamed", additions:int, deletions:int, old_path:null|string}`; (b) add top-level `total_additions:int` and `total_deletions:int` summary fields; (c) keep `staged` and `unstaged` raw strings as optional verbatim fields (e.g. under `raw_staged`, `raw_unstaged`) for callers that need the full text; (d) add regression coverage proving `diff --output-format json` in a workspace with changes includes a `files[]` array with at least one entry containing `path` and `status` fields. **Why this matters:** diff inspection is a key control-plane signal for claws deciding whether to commit, what to commit, or whether user-edited files need re-analysis. If the only machine-readable diff signal is a raw unified diff string, every orchestration layer must bundle a full diff parser, re-deriving what `git diff --stat` would have given for free. Source: Jobdori live dogfood, `e939777f`, 2026-05-01.