feat(remote): wake a sleeping host when a session is created or attached

Pressing Run on a remote case whose host was asleep failed with
`could not verify tmux on remote host 192.168.50.137: …` — an ssh error that
blames tmux for a machine that is merely suspended. The only wake paths were
typed input on an established session and the banner's Wake button, so OPENING a
session (the moment the user actually decides to use that host) had none.

`RemoteWakeRegistry.ensureHostAwake()` reuses the existing probe/wake/readiness
machinery for a host that has no session yet, and is wired into the two
user-initiated create paths: `POST /api/quick-start` for a remote case (before
the tmux prereq probe, which is what surfaced the misleading error) and
`POST /api/sessions` with `attachRemoteSession`. A host without a wake target is
not even probed, so its behavior and latency are byte-identical. The wake is
blocking — the caller gets the session or an error — but bounded by
REMOTE_WAKE_REQUEST_READY_TIMEOUT_MS (40 s) instead of the 90 s session default,
because the dashboard sits behind a reverse proxy whose default
`proxy_read_timeout` is 60 s: a longer wait would be cut off at the proxy while
the session was still being created. The budget has to cover the whole request
(40 s wake + 1.5 s probe + the tmux probe's own 15 s = 56.5 s worst case), which
is why it is 40 s and not 45. A timeout now says the host did not come back, and
an unreachable host without a wake target says so instead of pointing at tmux.

The wiring is deliberately in the HTTP ROUTE, never in the shared session
service: `cron-service.ts` builds sessions there with nobody waiting on the
answer, and a wake on that path would power the host on for every schedule —
the timer-driven re-wake invariant #1 exists to prevent. Both halves are asserted
(importers of `remote-wake`, and `ensureHostAwake` having exactly one caller
file), so a future caller has to come through the guard test. A rejection from
the wake IO is caught too: a broken target must fail the wake, not the route.

`remote:hostWaking`/`remote:hostWakeFailed` now carry `forNewSession` for the
session-less case, where "input is queued" would be untrue; the toast then reads
"the session starts when it is back".

Live wake numbers are unchanged (this reuses the measured ~12 s S3 path); the
route behavior is covered by new tests in session-routes.test.ts with an injected
registry, so no test opens a real socket or ssh.

docs/architecture-invariants.md

@@ -54,7 +54,7 @@ Model is NOT a session field: it is a composition entry in the profile's config
 
 ### Remote SSH cases
 
-**Remote host wake-on-LAN from user input**: an optional `RemoteHost.wakeMac` (magic packet built and broadcast by Codeman) or `RemoteHost.wakeCommand` (a single executable path, run WITHOUT a shell, and the explicit override) lets the input route — and an explicit `POST /api/sessions/:id/wake` — wake a SLEEPING host instead of writing into a stalled ssh pane; `tmux send-keys` succeeds against a stalled pane, so the bytes used to vanish silently. The wake flow lives in `src/remote-wake.ts` and is reachable **only** from `POST /api/sessions/:id/input` and that explicit wake route: the COD-108 auto-reconnect watcher, `Server.handleRemoteSessionDropped` and boot recovery must never wake a host, or it would be re-woken seconds after each suspend and could never stay asleep (asserted by a wiring guard in `test/remote-wake.test.ts`, not just documented). `GET /api/sessions/:id/reachability` only ASKS — it never wakes — and feeds the amber "host unreachable" banner (`host-wake-ui.js`) whose action is either Wake or, with no target configured, "Configure WoL" → `#wakeConfigModal` (saved via `PUT /api/remote-hosts/:id`). Detection is a throttled bare TCP probe (no ssh, no `ServerAliveInterval` — keepalives would move bytes into an idle connection every interval), input is buffered and flushed in order after `reattachRemote()` (the send-and-wait path blocks instead), and the wake fields are re-read from `remote-hosts.json` on recovery AND (throttled, cached) live for a running session, because the persisted `remote` snapshot would never see a field added later (`rehydrateRemoteHostFields` + `RemoteWakeDeps.resolveRemote`). Design + invariants: `docs/remote-sessions.md` §Wake-on-LAN from user input.
+**Remote host wake-on-LAN from user input**: an optional `RemoteHost.wakeMac` (magic packet built and broadcast by Codeman) or `RemoteHost.wakeCommand` (a single executable path, run WITHOUT a shell, and the explicit override) lets the input route — and an explicit `POST /api/sessions/:id/wake` — wake a SLEEPING host instead of writing into a stalled ssh pane; `tmux send-keys` succeeds against a stalled pane, so the bytes used to vanish silently. The wake flow lives in `src/remote-wake.ts` and is reachable **only** from an EXPLICIT user request: `POST /api/sessions/:id/input`, that explicit wake route, and the create/attach path (`POST /api/quick-start` for a remote case, `POST /api/sessions` with `attachRemoteSession`, via `ensureHostAwake`), because "the user pressed Run on a sleeping host" is the same kind of request and the tmux probe would otherwise fail with a misleading "needs tmux installed". Everything TIMER-driven must never wake a host: the COD-108 auto-reconnect watcher, `Server.handleRemoteSessionDropped` and boot recovery have no access to the registry, or a host would be re-woken seconds after each suspend and could never stay asleep (asserted by wiring guards in `test/remote-wake.test.ts`, not just documented — including that `ensureHostAwake` is called from the HTTP route only, since `cron-service.ts` builds sessions through the shared service with nobody waiting on the answer). `GET /api/sessions/:id/reachability` only ASKS — it never wakes — and feeds the amber "host unreachable" banner (`host-wake-ui.js`) whose action is either Wake or, with no target configured, "Configure WoL" → `#wakeConfigModal` (saved via `PUT /api/remote-hosts/:id`). Detection is a throttled bare TCP probe (no ssh, no `ServerAliveInterval` — keepalives would move bytes into an idle connection every interval), input is buffered and flushed in order after `reattachRemote()` (the send-and-wait path blocks instead, as does the create path, with a shorter request budget), and the wake fields are re-read from `remote-hosts.json` on recovery AND (throttled, cached) live for a running session, because the persisted `remote` snapshot would never see a field added later (`rehydrateRemoteHostFields` + `RemoteWakeDeps.resolveRemote`). Design + invariants: `docs/remote-sessions.md` §Wake-on-LAN from user input.
 
 **Remote SSH cases** (COD-94/#145): cases can point at a **remote host** (`~/.codeman/remote-hosts.json` + `remote-cases.json` via `src/remote-hosts.ts`; CRUD under `/api/cases` — cases route file). A remote session launches a LOCAL tmux pane running `ssh <host>` that creates a durable REMOTE tmux session on a **dedicated socket** `-L codeman-remote` with name `codeman-ssh-<id>` — deliberately failing the remote Codeman's `SAFE_MUX_NAME_PATTERN` so a Codeman instance on the target host never adopts it; no `-g` global tmux options are set remotely. `remotePath`/`identityFile` are schema-guarded against shell injection (backticks/`$` rejected — same approach as `extraSshOptions`); remote tmux availability is probed via `checkRemoteTmuxAvailable()` in quick-start (ssh args carry `-o ConnectTimeout=10`). Remote claude defaults to an idempotent `claude --session-id <id> || claude --resume <id>` pair under a login shell, so a respawn or reattach continues the SAME conversation rather than starting a fresh one (remote omp gets the same treatment via `--continue`; ⚠️ because the claude arm is an `a || b` pair under `-c`, that pane's PID is the login shell, not the agent); per-host `commands.*` override. Session kill best-effort kills the remote tmux too. `SessionState.remote`/`MuxSession.remote` round-trip through recovery (`restoreMuxSessions` passes `remote` back into the Session constructor). ⚠️ Run flows must route remote cases through `POST /api/quick-start` (which resolves the remote case and skips LOCAL CLI availability gates) — `POST /api/sessions` stat-validates `workingDir` locally and has no `caseName`. `envOverrides`/`effort`/`modelOverride`/`codexConfig`/`geminiConfig` are rejected for remote quick-starts (not silently dropped). UI: Create Case modal → Remote tab. Tests: `test/remote-hosts.test.ts`, `test/remote-ssh-options.test.ts`. ⚠️ **Reading a file in a remote case goes over ssh too** (#415): `src/remote-files.ts` is the single remote-READ layer (`buildRemoteFileCommand` = `buildSshConnectionArgs` + one shellescaped remote command; `remoteProbePaths` returns remote realpath + stat; `remoteCreateReadStream` streams a `Range` via `tail -c +N | head -c L` and its `close()` must be wired to the response's `close` or the ssh child outlives an aborted download). The guard order matches the local path exactly (`validateSessionFilePathLexical` → remote realpath of BOTH file and workspace root → containment → sensitive-path → size cap on the REMOTE size), a request path arrives from the browser and is only ever interpolated as a `shellescape`d token, and an unreachable host answers **502**, never a 404. ⚠️ The probe's symlink resolution FAILS CLOSED: `readlink -f` where it exists, otherwise a `cd -P`/`pwd -P` directory walk plus a bounded plain-`readlink` loop over the last component, and anything it cannot fully resolve is reported unresolvable (404), never as the unresolved string — the first version resolved the directory chain only, so on a host without `readlink -f` a `ws/notes.txt -> ~/.ssh/id_rsa` link passed containment under its own path while `cat` served the key. Records are NUL-separated and index-keyed so a newline in a filename cannot shift the mapping. ⚠️ ssh children are BOUNDED: probes and buffered reads go through `src/remote-ssh-limiter.ts` (a `document-conversion-limiter`-shaped semaphore, default 4), the attachment-history list probes its whole history in ONE batched call (`probeRemoteAttachmentHistory`, threaded into `registerExternalAttachment({remoteProbes})`), and probes chunk at 40 paths — a prompt-injected agent printing `codeman://attach` links in a remote session used to fork one `ssh` per link. `describeExecError` never returns Node's `Command failed: <ssh line>` message (identity path + probe script in a 502 body). The `PUT /file-content` guard sits AHEAD of `validateSessionFilePath`, which resolves LOCALLY, or a same-named local directory (an sshfs mount) takes the write. Under `VITEST` the three IO functions refuse rather than connect. This covers the ATTACHMENT routes too, which is the half a clicked path needs when the file is OUTSIDE the case directory (`_isExternalPreviewPath` sends it to `POST …/attachments`): registration, by-id `raw`, metadata and the history list all resolve over ssh (`registerExternalAttachment({remote})`, `resolveServableRemoteAttachment`), and what decides the host is the SESSION, never the path string — the same absolute path means a different file on each host. Deliberately NOT supported over ssh: writes (`edit=1`/`PUT` answer 400, `editable` is always false), office previews/thumbnails, the file tree/picker, `tail-file`. Tests: `test/remote-files.test.ts`, `test/routes/file-routes-remote.test.ts`.
 

docs/remote-sessions.md

@@ -368,6 +368,20 @@ it is unreachable it wakes it, polls until the host answers, reattaches the pane
 agent conversation is not restarted), and flushes the input that arrived meanwhile.
 Implementation: `src/remote-wake.ts`.
 
+The same wake path also serves **opening** a session, which is where a sleeping host used to
+be a dead end: pressing Run on a remote case (`POST /api/quick-start`) or Attach on a
+discovered remote tmux session (`POST /api/sessions` + `attachRemoteSession`) probes the host
+first, and on a sleeping one wakes it, waits for SSH and only then runs the tmux prereq probe.
+Without that the run failed with `could not verify tmux on remote host …` — an ssh error that
+blames tmux for a machine that is merely suspended. The wait is **blocking** (the caller gets
+the session or the error) but bounded by `REMOTE_WAKE_REQUEST_READY_TIMEOUT_MS` (40 s) rather
+than the 90 s session default, because the dashboard sits behind a reverse proxy whose default
+`proxy_read_timeout` is 60 s: a longer wait would be cut off at the proxy while the session was
+still being created. The budget covers the whole request, not just the wait (40 s wake + 1.5 s
+probe + the tmux prereq probe's own 15 s timeout = 56.5 s worst case). A host with no wake target is not even probed on this path, so nothing
+changes for it, and `remote:hostWaking` is broadcast without a `sessionId` (the toast then reads
+"the session starts when it is back" — there is no session yet, and no input queued behind it).
+
 Two wake paths, `wakeCommand` first because it is the explicit override:
 
 - **`wakeMac`** — Codeman builds the magic packet itself (`buildMagicPacket`, six `0xFF`
@@ -387,12 +401,17 @@ banner comes from `GET /api/sessions/:id/reachability`, polled for the active re
 
 The invariants worth keeping:
 
-- **Only real user input or an explicit wake request may wake a host.** The COD-108 watcher,
-  the server's dropped-session handler and boot recovery have no access to the wake registry —
-  a wake there would re-wake the host seconds after every suspend, so it could never stay
-  asleep (the same failure `hufflepuff-mcp-lazy` exists to prevent for MCP keepalives). A
-  reachability check never wakes: it is a question, not an action. Both are enforced by tests
-  in `test/remote-wake.test.ts` and `test/routes/session-remote-wake.test.ts`, not comments.
+- **Only an EXPLICIT request may wake a host:** user input on an established session, the wake
+  button, or the user's own session create/attach request (`ensureHostAwake`). Everything that
+  runs on a TIMER must never wake one — the COD-108 watcher, the server's dropped-session
+  handler, boot recovery and session discovery have no access to the wake registry, and neither
+  has the shared session service, because `cron-service.ts` builds sessions there with nobody
+  waiting on the answer; a wake on such a path would re-wake the host seconds after every
+  suspend, so it could never stay asleep (the same failure `hufflepuff-mcp-lazy` exists to
+  prevent for MCP keepalives). A reachability check, a discovery listing and the tmux prereq
+  probe never wake: they are questions, not actions. All of it is enforced by tests in
+  `test/remote-wake.test.ts` (two wiring guards, one of them asserting `ensureHostAwake` has
+  exactly one caller file) and `test/routes/session-remote-wake.test.ts`, not by comments.
 - **Detection is a bare TCP connect** to the SSH port (then the configured `port`, else 22),
   throttled per session, and only for wake-enabled hosts. No `ServerAliveInterval` is added to
   the launch command: keepalives push bytes into an otherwise idle connection every interval,

src/remote-wake.ts

@@ -8,11 +8,16 @@
  * lost with no error anywhere — the failure this module exists to close.
  *
  * Design (deliberately narrow, see docs/remote-sessions.md §Wake-on-LAN):
- *  - ONLY real user input wakes a host. The auto-reconnect watcher and
- *    boot-recovery must never wake one, or a host would be re-woken ~45 s after
- *    each suspend and could never stay asleep (the "keepalive pings a sleeping
- *    host" failure already solved for a different consumer by
- *    `hufflepuff-mcp-lazy`).
+ *  - An EXPLICIT request wakes a host, and nothing else: user input on an
+ *    established session (`handleInput`), the wake button (`ensureAwake`), or the
+ *    user's own session create/attach request (`ensureHostAwake`, wired in the HTTP
+ *    routes). Everything that runs on a TIMER — the auto-reconnect watcher, boot
+ *    recovery, the reachability probe, session discovery — must never wake one, or
+ *    a host would be re-woken ~45 s after each suspend and could never stay asleep
+ *    (the "keepalive pings a sleeping host" failure already solved for a different
+ *    consumer by `hufflepuff-mcp-lazy`). The create path is deliberately wired in
+ *    `session-routes.ts` and NOT in the shared session service, because
+ *    `cron-service.ts` builds sessions there without a user waiting on the answer.
  *  - Detection is a cheap TCP connect to the SSH port (no auth, no ssh client,
  *    a few hundred bytes — below any meaningful activity threshold), throttled
  *    per session. No SSH keepalive is added to the launch command: keepalives
@@ -41,6 +46,17 @@ export const REMOTE_WAKE_PROBE_TIMEOUT_MS = 1_500;
 export const REMOTE_WAKE_READY_INTERVAL_MS = 1_500;
 /** Bounded wait for the host to come back after the wake command ran. */
 export const REMOTE_WAKE_READY_TIMEOUT_MS = 90_000;
+/**
+ * Budget for a wake that an HTTP REQUEST is waiting on (session create/attach).
+ * Deliberately shorter than {@link REMOTE_WAKE_READY_TIMEOUT_MS}: the dashboard is
+ * served through a reverse proxy whose default `proxy_read_timeout` is 60 s, so a
+ * 90 s wait would be cut off AT THE PROXY while the session was still being built —
+ * the browser reports a failure for a session that exists. The budget has to cover
+ * the WHOLE request, not just the wait: 40 s here + the 1.5 s reachability probe +
+ * the tmux prereq probe's own 15 s timeout = 56.5 s worst case, still under 60 s.
+ * A warm S3 resume measures ~12 s, so 40 s is >3× the observed wake.
+ */
+export const REMOTE_WAKE_REQUEST_READY_TIMEOUT_MS = 40_000;
 /** The wake command itself must not hang the wake flow. */
 export const REMOTE_WAKE_COMMAND_TIMEOUT_MS = 10_000;
 /**
@@ -224,7 +240,7 @@ export interface RemoteWakeDeps {
   /** Run the resolved wake target (magic packet or host command). Resolves false on failure. */
   wake(target: NonNullable<WakeTarget>): Promise<boolean>;
   /** Poll until the woken host accepts connections again. */
-  waitUntilReady(remote: WakeableRemote): Promise<boolean>;
+  waitUntilReady(remote: WakeableRemote, opts?: { timeoutMs?: number }): Promise<boolean>;
   /** Sleep helper (injected for tests). */
   delay(ms: number): Promise<void>;
   /** Notify the COD-108 watcher so an exhausted backoff is reset. */
@@ -264,6 +280,25 @@ export function wakeConfigured(remote: WakeableRemote | undefined): WakeConfigur
   return target.kind;
 }
 
+/**
+ * Outcome of waking a host for a caller that has NO session yet (the create/attach
+ * routes). A union rather than a boolean because the three cases need different
+ * handling: `'no-target'` must leave the caller's behavior byte-identical (no probe,
+ * no extra latency for a host without WoL), and only `'failed'` is an error that
+ * deserves its own message instead of the caller's usual one.
+ */
+export type HostWakeOutcome = 'no-target' | 'ready' | 'failed';
+
+/**
+ * State key for a host-scoped wake. Prefixed so it can never collide with a session
+ * id, and keyed on the HOST rather than the case: two cases on one host share a
+ * single in-flight wake and one probe verdict. Such an entry is tiny (no input
+ * buffer) and bounded by the number of configured hosts, so it is never dropped.
+ */
+function hostWakeKey(hostId: string): string {
+  return `host:${hostId}`;
+}
+
 /** Per-session wake bookkeeping. */
 interface WakeState {
   probedAt: number;
@@ -391,6 +426,67 @@ export class RemoteWakeRegistry {
     return this.wake(session);
   }
 
+  /**
+   * Host-scoped reachability, for a caller that has no session yet (create/attach).
+   * Shares the per-HOST probe state with {@link ensureHostAwake}, so the probe the
+   * wake flow just paid for also answers "was that ssh failure really a sleeping
+   * machine?". Never wakes anything — it is a question, not an action.
+   */
+  async checkHostReachable(remote: WakeableRemote, opts: { force?: boolean; ttlMs?: number } = {}): Promise<boolean> {
+    const state = this._state(hostWakeKey(remote.hostId));
+    const ttl = opts.force ? 0 : (opts.ttlMs ?? REMOTE_WAKE_REACHABILITY_TTL_MS);
+    if (Date.now() - state.probedAt >= ttl) {
+      state.probedAt = Date.now();
+      state.reachable = await this.deps.probe(remote);
+    }
+    return state.reachable === true;
+  }
+
+  /**
+   * Wake a host for a REQUEST that is waiting on it — the session create/attach
+   * routes, where there is no session to reattach and no input to buffer yet.
+   *
+   * `'no-target'` returns without probing, so a host without WoL config costs
+   * nothing and behaves exactly as before. Single-flight per host, so a double click
+   * (or two cases on the same host) sends one packet and shares one readiness poll.
+   */
+  async ensureHostAwake(remote: WakeableRemote, opts: { timeoutMs?: number } = {}): Promise<HostWakeOutcome> {
+    if (!resolveWakeTarget(remote)) return 'no-target';
+    const state = this._state(hostWakeKey(remote.hostId));
+    if (state.waking) return (await state.waking) ? 'ready' : 'failed';
+
+    state.probedAt = Date.now();
+    state.reachable = await this.deps.probe(remote);
+    if (state.reachable) return 'ready';
+    this.deps.log?.(`[RemoteWake] ${remote.label} (${remote.host}) is unreachable — waking it for a new session`);
+    return (await this.wakeHost(remote, opts)) ? 'ready' : 'failed';
+  }
+
+  /**
+   * Single-flight wake for a host with no session (see {@link ensureHostAwake}).
+   * A write into the same `waking` slot the session flow uses, so the two can never
+   * run two readiness polls against one host from the same key space.
+   */
+  private async wakeHost(remote: WakeableRemote, opts: { timeoutMs?: number }): Promise<boolean> {
+    const state = this._state(hostWakeKey(remote.hostId));
+    if (state.waking) return state.waking;
+    state.waking = (async (): Promise<boolean> => {
+      try {
+        return await this._wakeAndWait(remote, state, { timeoutMs: opts.timeoutMs, forNewSession: true });
+      } catch (err) {
+        // Injected IO is documented not to throw, but a rejected promise here would
+        // surface as an unhandled rejection AND take the route down with it (the
+        // session path catches for exactly this reason). A broken wake target must
+        // fail the wake, never the create route beyond its own error response.
+        this.deps.log?.(`[RemoteWake] unexpected failure: ${err instanceof Error ? err.message : String(err)}`);
+        return false;
+      } finally {
+        state.waking = null;
+      }
+    })();
+    return state.waking;
+  }
+
   /**
    * Single-flight wake: probe-free (the caller already knows the host is down),
    * run the wake command, poll for readiness, reattach the pane, flush the buffer.
@@ -405,29 +501,9 @@ export class RemoteWakeRegistry {
     state.waking = (async (): Promise<boolean> => {
       const id = session.id;
       try {
-        this.deps.broadcast?.('remote:hostWaking', { sessionId: id, hostId: remote.hostId, label: remote.label });
-        this.deps.log?.(`[RemoteWake] waking ${remote.label} (${remote.host}) via ${target.kind} for session ${id}`);
+        const ready = await this._wakeAndWait(remote, state, { sessionId: id });
+        if (!ready) return false;
 
-        const woke = await this.deps.wake(target);
-        if (!woke) {
-          this.deps.log?.(
-            `[RemoteWake] wake failed for ${remote.label}: ${target.kind === 'command' ? target.command : 'magic packet'}`
-          );
-        }
-
-        const ready = await this.deps.waitUntilReady(remote);
-        if (!ready) {
-          this.deps.log?.(`[RemoteWake] ${remote.label} did not come back — input stays buffered`);
-          this.deps.broadcast?.('remote:hostWakeFailed', { sessionId: id, hostId: remote.hostId, label: remote.label });
-          // Reset the probe state so the NEXT user input probes and retries
-          // instead of trusting a stale "down" verdict forever.
-          state.probedAt = 0;
-          state.reachable = undefined;
-          return false;
-        }
-
-        state.reachable = true;
-        state.probedAt = Date.now();
         const reattached = await session.reattachRemote();
         if (!reattached) {
           this.deps.log?.(`[RemoteWake] ${remote.label} is up but the pane could not be reattached`);
@@ -453,6 +529,57 @@ export class RemoteWakeRegistry {
     return state.waking;
   }
 
+  /**
+   * Broadcast + run the wake target + wait for SSH. Shared by the session flow (which
+   * then reattaches and flushes the buffer) and the create/attach flow (which has no
+   * pane yet). On failure the probe state is reset so the NEXT attempt probes and
+   * retries instead of trusting a stale "down" verdict forever.
+   */
+  private async _wakeAndWait(
+    remote: WakeableRemote,
+    state: WakeState,
+    opts: { sessionId?: string; timeoutMs?: number; forNewSession?: boolean } = {}
+  ): Promise<boolean> {
+    const target = resolveWakeTarget(remote);
+    if (!target) return true;
+    const forWhat = opts.sessionId ? `for session ${opts.sessionId}` : 'for a new session';
+    // No `sessionId` for a create-path wake: the toast handler is then the only one
+    // that acts (a banner for a session that does not exist yet would have no target),
+    // which is exactly the `forNewSession` distinction the UI renders.
+    this.deps.broadcast?.('remote:hostWaking', {
+      ...(opts.sessionId ? { sessionId: opts.sessionId } : { forNewSession: true }),
+      hostId: remote.hostId,
+      label: remote.label,
+    });
+    this.deps.log?.(`[RemoteWake] waking ${remote.label} (${remote.host}) via ${target.kind} ${forWhat}`);
+
+    const woke = await this.deps.wake(target);
+    if (!woke) {
+      this.deps.log?.(
+        `[RemoteWake] wake failed for ${remote.label}: ${target.kind === 'command' ? target.command : 'magic packet'}`
+      );
+    }
+
+    const ready = await this.deps.waitUntilReady(remote, { timeoutMs: opts.timeoutMs });
+    if (!ready) {
+      this.deps.log?.(
+        `[RemoteWake] ${remote.label} did not come back — ${opts.forNewSession ? 'the session was not started' : 'input stays buffered'}`
+      );
+      this.deps.broadcast?.('remote:hostWakeFailed', {
+        ...(opts.sessionId ? { sessionId: opts.sessionId } : { forNewSession: true }),
+        hostId: remote.hostId,
+        label: remote.label,
+      });
+      state.probedAt = 0;
+      state.reachable = undefined;
+      return false;
+    }
+
+    state.reachable = true;
+    state.probedAt = Date.now();
+    return true;
+  }
+
   private _state(sessionId: string): WakeState {
     let state = this.states.get(sessionId);
     if (!state) {
@@ -675,7 +802,7 @@ export function createDefaultRemoteWakeDeps(overrides: Partial<RemoteWakeDeps> =
   return {
     probe: probeRemoteHostReachable,
     wake: (target) => (target.kind === 'command' ? runRemoteWakeCommand(target.command) : sendWakePackets(target.macs)),
-    waitUntilReady: (remote) => waitUntilRemoteReady(remote),
+    waitUntilReady: (remote, opts) => waitUntilRemoteReady(remote, opts),
     delay,
     ...overrides,
   };

src/web/public/host-wake-ui.js

@@ -326,9 +326,16 @@ Object.assign(CodemanApp.prototype, {
    */
   _onRemoteHostWaking(data) {
     const label = data && data.label ? data.label : 'Remote host';
+    // A create-path wake (the user pressed Run / Attach) has no session yet, so
+    // nothing is queued behind it — the wording has to say what actually happens.
+    const forNewSession = Boolean(data && data.forNewSession);
     // Long enough to cover the wake + attach (~10s measured on a warm S3), and it
     // is replaced by `remote:sessionReconnected` the moment the pane is back.
-    this.showToast(`Waking ${label} … input is queued`, 'info', { duration: 12000 });
+    this.showToast(
+      forNewSession ? `Waking ${label} … the session starts when it is back` : `Waking ${label} … input is queued`,
+      'info',
+      { duration: 12000 }
+    );
     const state = this._hostWake;
     if (!state || !data || state.sessionId !== data.sessionId) return;
     state.waking = true;
@@ -340,7 +347,14 @@ Object.assign(CodemanApp.prototype, {
   /** SSE `remote:hostWakeFailed` — the host did not come back in time. */
   _onRemoteHostWakeFailed(data) {
     const label = data && data.label ? data.label : 'Remote host';
-    this.showToast(`${label} did not wake up — queued input is still held`, 'error', { duration: 15000 });
+    const forNewSession = Boolean(data && data.forNewSession);
+    this.showToast(
+      forNewSession
+        ? `${label} did not wake up — no session was started`
+        : `${label} did not wake up — queued input is still held`,
+      'error',
+      { duration: 15000 }
+    );
     const state = this._hostWake;
     if (!state || !data || state.sessionId !== data.sessionId) return;
     state.waking = false;

src/web/routes/session-routes.ts

@@ -28,6 +28,7 @@ import {
   type GrokConfig,
   type DeepSeekConfig,
   type OmpConfig,
+  type RemoteHost,
 } from '../../types.js';
 import { Session, isAltScreenStripMode, isExternalCliMode, isMuxAltScreenOnlyStripMode } from '../../session.js';
 import { SseEvent } from '../sse-events.js';
@@ -67,7 +68,12 @@ import {
   type WaitSignal,
   type SignalWaitResult,
 } from '../session-wait-registry.js';
-import { RemoteWakeRegistry, createDefaultRemoteWakeDeps } from '../../remote-wake.js';
+import {
+  RemoteWakeRegistry,
+  REMOTE_WAKE_REQUEST_READY_TIMEOUT_MS,
+  createDefaultRemoteWakeDeps,
+  type WakeableRemote,
+} from '../../remote-wake.js';
 import { clampWaitMs, MAX_BUFFER_SCAN_BYTES } from '../../config/agent-wait.js';
 import {
   autoConfigureRalph,
@@ -816,6 +822,22 @@ export function resolveOmpConfigForCreate(
   return resolvedId ? { ...ompConfig, resumeSessionId: resolvedId } : ompConfig;
 }
 
+/**
+ * `RemoteHost` → the wake registry's host shape. They differ in one field name only
+ * (`id` in host config vs `hostId` on a session's `remote`), but the rename is load-
+ * bearing: the registry keys its per-host wake state on `hostId`.
+ */
+function wakeableHost(host: RemoteHost): WakeableRemote {
+  return {
+    hostId: host.id,
+    label: host.label,
+    host: host.host,
+    port: host.port,
+    wakeMac: host.wakeMac,
+    wakeCommand: host.wakeCommand,
+  };
+}
+
 export function registerSessionRoutes(
   app: FastifyInstance,
   ctx: SessionPort & EventPort & ConfigPort & InfraPort & AuthPort & TabLayoutPort,
@@ -928,6 +950,19 @@ export function registerSessionRoutes(
       const { hostId, remoteSessionName } = body.attachRemoteSession;
       const host = (await readRemoteHosts(CODEMAN_CONFIG_DIR)).find((item) => item.id === hostId);
       if (!host) return createErrorResponse(ApiErrorCode.NOT_FOUND, 'Remote host not found');
+      // An explicit wake request is the only thing that may wake a host, and the user
+      // pressing Attach IS one (see quick-start for the same gate, and
+      // `remote-wake.ts` for what must never call this). Without it a sleeping host
+      // answers with an ssh failure that blames anything but the machine being asleep.
+      const hostWake = await remoteWake.ensureHostAwake(wakeableHost(host), {
+        timeoutMs: REMOTE_WAKE_REQUEST_READY_TIMEOUT_MS,
+      });
+      if (hostWake === 'failed') {
+        return createErrorResponse(
+          ApiErrorCode.OPERATION_FAILED,
+          `${host.label} did not come back after a wake-on-LAN request — nothing was attached`
+        );
+      }
       workingDir = `${host.username}@${host.host}:${remoteSessionName}`;
       remote = toAttachedSessionRemote(host, remoteSessionName, workingDir);
     }
@@ -3272,11 +3307,39 @@ export function registerSessionRoutes(
         );
       }
 
+      // The user pressing "Run" on a case whose host is asleep IS an explicit wake
+      // request (docs/remote-sessions.md §Wake-on-LAN), and the tmux probe below would
+      // otherwise fail with "could not verify tmux on remote host …" — an ssh failure
+      // that blames tmux for a machine that is merely suspended. Wired HERE, in the HTTP
+      // route, and deliberately NOT in the shared session service: `cron-service.ts`
+      // builds sessions through the service, and a wake down there would re-wake the
+      // host on every schedule (the failure invariant #1 exists to prevent).
+      const hostWake = await remoteWake.ensureHostAwake(wakeableHost(host), {
+        timeoutMs: REMOTE_WAKE_REQUEST_READY_TIMEOUT_MS,
+      });
+      if (hostWake === 'failed') {
+        return createErrorResponse(
+          ApiErrorCode.OPERATION_FAILED,
+          `${host.label} did not come back after a wake-on-LAN request — the session was not started`
+        );
+      }
+
       // tmux is a hard prerequisite on the remote host (the agent runs inside a remote
       // tmux server so it survives ssh drops). Probe before spawning so a missing tmux
       // surfaces a clear, structured error instead of a dead "tmux: command not found" pane.
       const tmuxCheck = await checkRemoteTmuxAvailable(host);
       if (!tmuxCheck.ok) {
+        // An unreachable host and a host without tmux fail the same way over ssh, so the
+        // probe's own message would send the user hunting for a tmux install. Ask the
+        // registry (which just probed, when it woke the host) which of the two it is.
+        if (!(await remoteWake.checkHostReachable(wakeableHost(host)))) {
+          return createErrorResponse(
+            ApiErrorCode.OPERATION_FAILED,
+            hostWake === 'no-target'
+              ? `${host.label} (${host.host}) is not reachable, and this host has no wake-on-LAN target — configure a MAC address or a wake command first`
+              : `${host.label} (${host.host}) is not reachable`
+          );
+        }
         return createErrorResponse(ApiErrorCode.OPERATION_FAILED, tmuxCheck.error || 'remote host is missing tmux');
       }
 

test/remote-wake.test.ts

@@ -26,6 +26,7 @@ import {
   sendWakePackets,
   wakeConfigured,
   REMOTE_WAKE_PENDING_MAX_BYTES,
+  REMOTE_WAKE_REQUEST_READY_TIMEOUT_MS,
   type RemoteWakeDeps,
   type WakeableRemote,
   type WakeableSession,
@@ -439,6 +440,98 @@ describe('RemoteWakeRegistry', () => {
   });
 });
 
+// ========== Host-scoped wake (session create/attach) ==========
+
+describe('RemoteWakeRegistry — host-scoped wake for a request that waits on it', () => {
+  const hostRemote: WakeableRemote = {
+    hostId: 'hufflepuff',
+    label: 'Hufflepuff',
+    host: '192.168.50.137',
+    wakeMac: '04:d9:f5:80:c6:58',
+  };
+
+  it('does not even probe a host without a wake target (byte-identical to no feature)', async () => {
+    const h = harness({ remote: { hostId: 'x', label: 'X', host: '10.0.0.9' } });
+    await expect(h.registry.ensureHostAwake(h.session.remote!)).resolves.toBe('no-target');
+    expect(h.probe).not.toHaveBeenCalled();
+    expect(h.wake).not.toHaveBeenCalled();
+  });
+
+  it('reports ready without waking when the host already answers', async () => {
+    const h = harness({ remote: hostRemote });
+    h.probe.mockResolvedValue(true);
+    await expect(h.registry.ensureHostAwake(hostRemote)).resolves.toBe('ready');
+    expect(h.wake).not.toHaveBeenCalled();
+  });
+
+  it('wakes a sleeping host and waits with the caller’s budget, not the 90 s default', async () => {
+    const h = harness({ remote: hostRemote });
+    h.probe.mockResolvedValue(false);
+
+    await expect(
+      h.registry.ensureHostAwake(hostRemote, { timeoutMs: REMOTE_WAKE_REQUEST_READY_TIMEOUT_MS })
+    ).resolves.toBe('ready');
+
+    expect(h.wake).toHaveBeenCalledWith({ kind: 'mac', macs: [[4, 217, 245, 128, 198, 88]] });
+    // The budget has to reach the readiness poll: the reverse proxy cuts a request at
+    // 60 s, so a create-path wake must not inherit the 90 s session default.
+    expect(h.waitUntilReady).toHaveBeenCalledWith(hostRemote, {
+      timeoutMs: REMOTE_WAKE_REQUEST_READY_TIMEOUT_MS,
+    });
+    expect(h.events).toContain('remote:hostWaking');
+  });
+
+  it('reports failed when the host never comes back, and probes again on the next attempt', async () => {
+    const h = harness({ remote: hostRemote });
+    h.probe.mockResolvedValue(false);
+    h.waitUntilReady.mockResolvedValue(false);
+
+    await expect(h.registry.ensureHostAwake(hostRemote)).resolves.toBe('failed');
+    expect(h.events).toContain('remote:hostWakeFailed');
+
+    // The failure resets the probe verdict, so a second Run probes instead of
+    // trusting a stale "down" forever.
+    h.waitUntilReady.mockResolvedValue(true);
+    h.probe.mockClear();
+    await expect(h.registry.ensureHostAwake(hostRemote)).resolves.toBe('ready');
+    expect(h.probe).toHaveBeenCalled();
+  });
+
+  it('single-flights two concurrent create-path wakes for the same host', async () => {
+    const h = harness({ remote: hostRemote });
+    h.probe.mockResolvedValue(false);
+    let release: (value: boolean) => void = () => {};
+    h.waitUntilReady.mockImplementation(() => new Promise<boolean>((resolve) => (release = resolve)));
+
+    const first = h.registry.ensureHostAwake(hostRemote);
+    const second = h.registry.ensureHostAwake(hostRemote);
+    await vi.waitFor(() => expect(h.wake).toHaveBeenCalledTimes(1));
+    release(true);
+
+    await expect(Promise.all([first, second])).resolves.toEqual(['ready', 'ready']);
+    // One magic packet for a double click, not two.
+    expect(h.wake).toHaveBeenCalledTimes(1);
+  });
+
+  it('checkHostReachable is a question, never an action', async () => {
+    const h = harness({ remote: hostRemote });
+    h.probe.mockResolvedValue(false);
+
+    await expect(h.registry.checkHostReachable(hostRemote)).resolves.toBe(false);
+    expect(h.wake).not.toHaveBeenCalled();
+  });
+
+  it('reports failed instead of rejecting when the wake IO itself throws', async () => {
+    // A create route must answer with its own error, not a 500 from an unexpected
+    // rejection — the session flow catches for the same reason.
+    const h = harness({ remote: hostRemote });
+    h.probe.mockResolvedValue(false);
+    h.wake.mockRejectedValue(new Error('udp socket exploded'));
+
+    await expect(h.registry.ensureHostAwake(hostRemote)).resolves.toBe('failed');
+  });
+});
+
 // ========== Wiring guard ==========
 
 const SRC = fileURLToPath(new URL('../src', import.meta.url));
@@ -468,4 +561,20 @@ describe('wake wiring guard', () => {
 
     expect(importers.sort()).toEqual([...allowed].sort());
   });
+
+  it('wakes a host for a create/attach request ONLY from the HTTP route', () => {
+    // The create-path wake (`ensureHostAwake`) is a USER request, so it belongs to the
+    // HTTP route. `cron-service.ts` builds sessions through the shared service with
+    // nobody waiting on the answer, so a wake down there would power the host on for
+    // every schedule — the failure invariant #1 exists to prevent. Asserted across the
+    // source tree, so a future caller has to come through this test.
+    // `remote-wake.ts` names itself: that is the definition, not a caller, and the
+    // import guard above already pins the file to the route.
+    const allowed = new Set([join('web', 'routes', 'session-routes.ts'), 'remote-wake.ts']);
+    const callers = walkTs(SRC)
+      .filter((full) => /ensureHostAwake\s*\(/.test(readFileSync(full, 'utf-8')))
+      .map((full) => relative(SRC, full));
+
+    expect(callers.sort()).toEqual([...allowed].sort());
+  });
 });

test/routes/session-routes.test.ts

@@ -55,6 +55,7 @@ vi.mock('../../src/remote-hosts.js', async (orig) => {
 });
 
 import { registerSessionRoutes } from '../../src/web/routes/session-routes.js';
+import { RemoteWakeRegistry, REMOTE_WAKE_REQUEST_READY_TIMEOUT_MS } from '../../src/remote-wake.js';
 import { resolveTerminalHistoryConfig } from '../../src/config/terminal-history.js';
 
 interface LocalHarness {
@@ -62,6 +63,15 @@ interface LocalHarness {
   ctx: MockRouteContext;
 }
 
+// Wake-on-LAN seam: the production registry opens a real TCP connection to the host
+// and can run a real wake command, so every route registered here gets a fake one
+// (the same seam `test/routes/session-remote-wake.test.ts` uses). Default: the host
+// answers, so nothing ever wakes.
+const wakeProbe = vi.fn(async () => true);
+const wakeCommandRun = vi.fn(async () => true);
+const wakeWaitUntilReady = vi.fn(async () => true);
+let wakeRegistry: RemoteWakeRegistry;
+
 /**
  * Build a Fastify instance that mirrors production's uniform-envelope behavior
  * (server.ts preSerialization hook) so the test wire format matches the contract:
@@ -108,7 +118,17 @@ describe('session-routes', () => {
   let harness: LocalHarness;
 
   beforeEach(async () => {
-    harness = await createEnvelopeHarness(registerSessionRoutes);
+    wakeProbe.mockReset().mockResolvedValue(true);
+    wakeCommandRun.mockReset().mockResolvedValue(true);
+    wakeWaitUntilReady.mockReset().mockResolvedValue(true);
+    wakeRegistry = new RemoteWakeRegistry({
+      probe: wakeProbe,
+      wake: wakeCommandRun,
+      waitUntilReady: wakeWaitUntilReady,
+      delay: async () => {},
+      log: () => {},
+    });
+    harness = await createEnvelopeHarness((app, ctx) => registerSessionRoutes(app, ctx, { remoteWake: wakeRegistry }));
     // Reset remote store so tests start with empty hosts/cases and a passing tmux probe
     remoteStore.hosts = [];
     remoteStore.cases = [];
@@ -1897,6 +1917,132 @@ describe('session-routes', () => {
       expect(JSON.parse(res.body)).toMatchObject({ success: false, errorCode: ApiErrorCode.OPERATION_FAILED });
     });
 
+    describe('remote create/attach wakes a sleeping host (Wake-on-LAN)', () => {
+      const host = (extra: Record<string, unknown> = {}) => ({
+        id: 'hufflepuff',
+        label: 'Hufflepuff',
+        host: '192.168.50.137',
+        username: 'j',
+        wakeMac: '04:d9:f5:80:c6:58',
+        ...extra,
+      });
+      const remoteCase = { name: 'hufflepuff-work', type: 'remote', hostId: 'hufflepuff', remotePath: '/home/j/work' };
+      const quickStart = () =>
+        harness.app.inject({
+          method: 'POST',
+          url: '/api/quick-start',
+          payload: { caseName: 'hufflepuff-work', mode: 'shell' },
+        });
+
+      it('wakes the host before the tmux probe when the user runs a remote case', async () => {
+        const startShell = vi.spyOn(Session.prototype, 'startShell').mockResolvedValue(undefined);
+        try {
+          remoteStore.hosts = [host()];
+          remoteStore.cases = [remoteCase];
+          wakeProbe.mockResolvedValue(false); // asleep
+
+          const res = await quickStart();
+
+          expect(res.statusCode).toBe(200);
+          expect(JSON.parse(res.body).success).toBe(true);
+          expect(wakeCommandRun).toHaveBeenCalledWith({ kind: 'mac', macs: [[4, 217, 245, 128, 198, 88]] });
+          // The request budget, not the 90 s session default: the reverse proxy would
+          // cut the request at 60 s while the session was still being built.
+          expect(wakeWaitUntilReady).toHaveBeenCalledWith(expect.objectContaining({ hostId: 'hufflepuff' }), {
+            timeoutMs: REMOTE_WAKE_REQUEST_READY_TIMEOUT_MS,
+          });
+        } finally {
+          startShell.mockRestore();
+        }
+      });
+
+      it('does not wake a host that answers, and never probes a host without a wake target', async () => {
+        const startShell = vi.spyOn(Session.prototype, 'startShell').mockResolvedValue(undefined);
+        try {
+          remoteStore.hosts = [host()];
+          remoteStore.cases = [remoteCase];
+          // The fake probe answers `true` by default — a reachable host.
+          expect((await quickStart()).statusCode).toBe(200);
+          expect(wakeCommandRun).not.toHaveBeenCalled();
+
+          // No wake target at all: not even a probe, so hosts without WoL keep the
+          // exact behavior (and latency) they had before this feature.
+          wakeProbe.mockClear();
+          remoteStore.hosts = [host({ wakeMac: undefined })];
+          expect((await quickStart()).statusCode).toBe(200);
+          expect(wakeProbe).not.toHaveBeenCalled();
+          expect(wakeCommandRun).not.toHaveBeenCalled();
+        } finally {
+          startShell.mockRestore();
+        }
+      });
+
+      it('refuses the run when the host never comes back, and starts no session', async () => {
+        remoteStore.hosts = [host()];
+        remoteStore.cases = [remoteCase];
+        wakeProbe.mockResolvedValue(false);
+        wakeWaitUntilReady.mockResolvedValue(false);
+        const sessionsBefore = harness.ctx.sessions.size;
+
+        const res = await quickStart();
+
+        expect(res.statusCode).toBe(httpStatusForErrorCode(ApiErrorCode.OPERATION_FAILED));
+        expect(JSON.parse(res.body).error).toMatch(/did not come back after a wake-on-LAN request/);
+        // No half-created session: the failure is the answer, not a dead tab.
+        expect(harness.ctx.sessions.size).toBe(sessionsBefore);
+      });
+
+      it('blames the sleeping host, not tmux, when the host has no wake target', async () => {
+        remoteStore.hosts = [host({ wakeMac: undefined })];
+        remoteStore.cases = [remoteCase];
+        remoteStore.tmuxCheck = {
+          ok: false,
+          error: 'remote host 192.168.50.137 needs tmux installed for durable remote sessions',
+        };
+        wakeProbe.mockResolvedValue(false);
+
+        const res = await quickStart();
+
+        expect(res.statusCode).toBe(httpStatusForErrorCode(ApiErrorCode.OPERATION_FAILED));
+        expect(JSON.parse(res.body).error).toMatch(/has no wake-on-LAN target/);
+      });
+
+      it('keeps the tmux error when the host is up but tmux is really missing', async () => {
+        remoteStore.hosts = [host()];
+        remoteStore.cases = [remoteCase];
+        remoteStore.tmuxCheck = {
+          ok: false,
+          error: 'remote host 192.168.50.137 needs tmux installed for durable remote sessions',
+        };
+        // Probe answers `true`: the ssh failure is genuinely about tmux.
+
+        const res = await quickStart();
+
+        expect(JSON.parse(res.body).error).toMatch(/needs tmux installed/);
+      });
+
+      it('wakes the host when attaching to a discovered remote session', async () => {
+        const startInteractive = vi.spyOn(Session.prototype, 'startInteractive').mockResolvedValue(undefined);
+        const startShell = vi.spyOn(Session.prototype, 'startShell').mockResolvedValue(undefined);
+        try {
+          remoteStore.hosts = [host()];
+          wakeProbe.mockResolvedValue(false);
+
+          const res = await harness.app.inject({
+            method: 'POST',
+            url: '/api/sessions',
+            payload: { attachRemoteSession: { hostId: 'hufflepuff', remoteSessionName: 'codeman-abc12345' } },
+          });
+
+          expect(res.statusCode).toBe(200);
+          expect(wakeCommandRun).toHaveBeenCalledTimes(1);
+        } finally {
+          startInteractive.mockRestore();
+          startShell.mockRestore();
+        }
+      });
+    });
+
     it('does not run local codex availability check for a remote codex case', async () => {
       // A remote codex case must NOT be blocked by the LOCAL codex availability gate
       // (the CLI runs on the remote host). Probe is stubbed ok in remoteStore.tmuxCheck.