fix(ssh): preserve terminal prompt observation deadlines

src/main/ssh/ssh-host-cli-deadline.ts

@@ -0,0 +1,43 @@
+import { parseRemoteCliArgs } from './ssh-remote-cli-args'
+import { clampOrchestrationAskTimeoutMs } from '../../shared/orchestration-ask-timeout'
+import {
+  isSafeTimerDelayMs,
+  parsePositiveSafeIntegerNumericText,
+  parsePositiveSafeIntegerText
+} from '../../shared/timer-delay'
+
+const DEFAULT_KILL_TIMEOUT_MS = 10 * 60_000
+const KILL_TIMEOUT_GRACE_MS = 2 * 60_000
+
+/** Kill timer for the host CLI subprocess. Long-poll commands carry their wait
+ * budget in `--timeout-ms`; extend past it so the CLI's own timeout fires
+ * first and produces a proper error message. */
+export function resolveHostCliKillTimeoutMs(argv: string[]): number {
+  const parsed = parseRemoteCliArgs(argv)
+  const rawTimeout = parsed.flags.get('timeout-ms')
+  if (parsed.commandPath[0] === 'terminal' && parsed.commandPath[1] === 'send') {
+    const rawWait = parsed.flags.get('wait-submit')
+    const seconds =
+      typeof rawWait === 'string' ? parsePositiveSafeIntegerNumericText(rawWait) : null
+    if (seconds !== null && seconds <= 3600) {
+      return Math.max(DEFAULT_KILL_TIMEOUT_MS, seconds * 1000 + KILL_TIMEOUT_GRACE_MS)
+    }
+  }
+  if (parsed.commandPath[0] === 'orchestration' && parsed.commandPath[1] === 'ask') {
+    const explicit =
+      typeof rawTimeout === 'string' ? parsePositiveSafeIntegerText(rawTimeout) : null
+    return Math.max(
+      DEFAULT_KILL_TIMEOUT_MS,
+      clampOrchestrationAskTimeoutMs(explicit ?? undefined) + KILL_TIMEOUT_GRACE_MS
+    )
+  }
+  const explicit =
+    typeof rawTimeout === 'string' ? parsePositiveSafeIntegerNumericText(rawTimeout) : null
+  // Why: this feeds the kill timer directly, so a post-grace budget outside the
+  // timer range degrades to the default instead of throwing at spawn time.
+  const extended = explicit === null ? null : explicit + KILL_TIMEOUT_GRACE_MS
+  if (extended !== null && isSafeTimerDelayMs(extended)) {
+    return Math.max(DEFAULT_KILL_TIMEOUT_MS, extended)
+  }
+  return DEFAULT_KILL_TIMEOUT_MS
+}

src/main/ssh/ssh-remote-cli-args.ts

@@ -1,3 +1,4 @@
+import { CLI_BOOLEAN_FLAGS } from '../../shared/cli-argument-boundary'
 import { RemoteCliArgumentError, type ParsedRemoteCli } from './ssh-remote-cli-argument-error'
 import {
   isOrchestrationRetryRequestId,
@@ -5,24 +6,6 @@ import {
   VALUELESS_RETRY_REQUEST_GUIDANCE
 } from '../../shared/orchestration-retry-request-id'
 
-const REMOTE_BOOLEAN_FLAGS = new Set([
-  'all',
-  'attachments',
-  'children',
-  'comments',
-  'current',
-  'full',
-  'help',
-  'inject',
-  'include-archived',
-  'include-visual-layouts',
-  'json',
-  'me',
-  'relations',
-  'parent-current',
-  'unread',
-  'wait'
-])
 const REPEATED_FLAG_SEPARATOR = '\u0000'
 const REPEATABLE_REMOTE_STRING_FLAGS = new Set(['label'])
 
@@ -121,7 +104,7 @@ export function optionalRemoteCliNumber(
 function isRemoteBooleanFlag(flag: string, commandPath: string[]): boolean {
   // Why: Android launch already uses --activity <name>; only Linear issue reads use it as a boolean.
   return (
-    REMOTE_BOOLEAN_FLAGS.has(flag) ||
+    CLI_BOOLEAN_FLAGS.has(flag) ||
     (flag === 'activity' && commandPath[0] === 'linear' && commandPath[1] === 'issue')
   )
 }

src/main/ssh/ssh-remote-cli-host-passthrough.test.ts

@@ -160,6 +160,27 @@ describe('buildHostCliEnv', () => {
 })
 
 describe('resolveHostCliKillTimeoutMs', () => {
+  it.each([
+    ['--wait-submit', '3600'],
+    ['--wait-submit=3600'],
+    ['--wait-submit=3600.000000000000001'],
+    ['--wait-submit', '1', '--wait-submit=3600']
+  ])('keeps SSH prompt observation inside both outer deadlines: %j', (...waitFlags) => {
+    const argv = ['terminal', 'send', '--text', 'review', '--enter', ...waitFlags]
+    const innerTimeout = 3_600_000 + 10_000
+    const hostTimeout = resolveHostCliKillTimeoutMs(argv)
+    const relayTimeout = remoteCliRequestTimeoutMs({ argv })!
+    expect(hostTimeout).toBeGreaterThan(innerTimeout)
+    expect(relayTimeout).toBeGreaterThan(hostTimeout)
+  })
+
+  it('keeps pre-command Enter flags inside the prompt observation deadline', () => {
+    const argv = ['--enter', 'terminal', 'send', '--text', 'review', '--wait-submit', '3600']
+    const hostTimeout = resolveHostCliKillTimeoutMs(argv)
+    expect(hostTimeout).toBeGreaterThan(3_610_000)
+    expect(remoteCliRequestTimeoutMs({ argv })).toBeGreaterThan(hostTimeout)
+  })
+
   it('extends the kill timer past an explicit --timeout-ms budget', () => {
     expect(resolveHostCliKillTimeoutMs(['terminal', 'wait', '--timeout-ms', '1800000'])).toBe(
       1_920_000

src/main/ssh/ssh-remote-cli-host-passthrough.ts

@@ -1,22 +1,12 @@
-// Why: the SSH relay shim (`~/.orca-relay/bin/orca`) forwards CLI invocations
-// to the host app. Instead of re-implementing every command in a hand-rolled
-// switch (the cause of "Unsupported SSH Orca CLI command", #7716), the host
-// runs the real bundled `orca` CLI entry in Electron node mode — the same
-// entry the local shell command uses — so remote invocations get the full
-// command surface (orchestration, worktree, terminal, ...) by construction.
+// The SSH shim runs the bundled CLI so remote shells get the full command surface.
 import { app } from 'electron'
 import { spawn as nodeSpawn } from 'node:child_process'
 import { existsSync } from 'node:fs'
 import { join } from 'node:path'
 import { getCanonicalUserDataPath } from '../persistence'
-import { parseRemoteCliArgs } from './ssh-remote-cli-args'
-import { clampOrchestrationAskTimeoutMs } from '../../shared/orchestration-ask-timeout'
-import {
-  MAX_TIMER_DELAY_MS,
-  isSafeTimerDelayMs,
-  parsePositiveSafeIntegerNumericText,
-  parsePositiveSafeIntegerText
-} from '../../shared/timer-delay'
+import { resolveHostCliKillTimeoutMs } from './ssh-host-cli-deadline'
+export { resolveHostCliKillTimeoutMs } from './ssh-host-cli-deadline'
+import { MAX_TIMER_DELAY_MS, isSafeTimerDelayMs } from '../../shared/timer-delay'
 import {
   ORCHESTRATION_COMPATIBILITY_ATTACHMENT_ENV,
   ORCHESTRATION_COMPATIBILITY_HOST_ID_ENV,
@@ -81,10 +71,7 @@ export type HostCliPassthroughOptions = {
  * working even on broken installs. */
 export class HostCliUnavailableError extends Error {}
 
-// Why: only Orca terminal-context vars may cross from the remote shell into
-// the host CLI process. Remote PATH / ORCA_USER_DATA_PATH are paths on the
-// remote machine (meaningless or instance-hijacking on the host), and
-// NODE_OPTIONS-style vars could alter host execution.
+// Only terminal identity may cross hosts; remote paths and Node options cannot.
 const REMOTE_CONTEXT_ENV_VARS = [
   'ORCA_TERMINAL_HANDLE',
   'ORCA_WORKTREE_ID',
@@ -93,11 +80,8 @@ const REMOTE_CONTEXT_ENV_VARS = [
   'ORCA_WORKSPACE_ID'
 ] as const
 
-// Why: bound captured output so a runaway command cannot balloon the relay
-// JSON-RPC response or main-process memory.
+// Bound output retained for the relay response.
 const MAX_CAPTURED_OUTPUT_BYTES = 8 * 1024 * 1024
-const DEFAULT_KILL_TIMEOUT_MS = 10 * 60_000
-const KILL_TIMEOUT_GRACE_MS = 2 * 60_000
 
 export function resolveHostCliEntryPath(app: {
   isPackaged: boolean
@@ -112,31 +96,6 @@ export function resolveHostCliEntryPath(app: {
     : join(app.appPath, 'out', 'cli', 'index.js')
 }
 
-/** Kill timer for the host CLI subprocess. Long-poll commands carry their wait
- * budget in `--timeout-ms`; extend past it so the CLI's own timeout fires
- * first and produces a proper error message. */
-export function resolveHostCliKillTimeoutMs(argv: string[]): number {
-  const parsed = parseRemoteCliArgs(argv)
-  const rawTimeout = parsed.flags.get('timeout-ms')
-  if (parsed.commandPath[0] === 'orchestration' && parsed.commandPath[1] === 'ask') {
-    const explicit =
-      typeof rawTimeout === 'string' ? parsePositiveSafeIntegerText(rawTimeout) : null
-    return Math.max(
-      DEFAULT_KILL_TIMEOUT_MS,
-      clampOrchestrationAskTimeoutMs(explicit ?? undefined) + KILL_TIMEOUT_GRACE_MS
-    )
-  }
-  const explicit =
-    typeof rawTimeout === 'string' ? parsePositiveSafeIntegerNumericText(rawTimeout) : null
-  // Why: this feeds the kill timer directly, so a post-grace budget outside the
-  // timer range degrades to the default instead of throwing at spawn time.
-  const extended = explicit === null ? null : explicit + KILL_TIMEOUT_GRACE_MS
-  if (extended !== null && isSafeTimerDelayMs(extended)) {
-    return Math.max(DEFAULT_KILL_TIMEOUT_MS, extended)
-  }
-  return DEFAULT_KILL_TIMEOUT_MS
-}
-
 export function buildHostCliEnv(args: {
   hostEnv: NodeJS.ProcessEnv
   remoteEnv: Record<string, string>

src/relay/remote-cli-timeout.ts

@@ -1,3 +1,4 @@
+import { CLI_BOOLEAN_FLAGS } from '../shared/cli-argument-boundary'
 import { clampOrchestrationAskTimeoutMs } from '../shared/orchestration-ask-timeout'
 import {
   isSafeTimerDelayMs,
@@ -14,23 +15,8 @@ import {
 const REMOTE_CLI_DEFAULT_TIMEOUT_MS = 5 * 60_000
 const REMOTE_CLI_WAIT_TIMEOUT_MS = 10 * 60_000
 const REMOTE_CLI_TIMEOUT_GRACE_MS = 60_000
-const ORCHESTRATION_ASK_RELAY_GRACE_MS = 3 * 60_000
-const ORCHESTRATION_ASK_RELAY_BASE_MS = 11 * 60_000
-
-const REMOTE_TIMEOUT_BOOLEAN_FLAGS = new Set([
-  'all',
-  'attachments',
-  'children',
-  'comments',
-  'current',
-  'full',
-  'help',
-  'inject',
-  'json',
-  'relations',
-  'unread',
-  'wait'
-])
+const REMOTE_CLI_LONG_WAIT_GRACE_MS = 3 * 60_000
+const REMOTE_CLI_LONG_WAIT_BASE_MS = 11 * 60_000
 
 export function remoteCliRequestTimeoutMs(params: Record<string, unknown>): number | undefined {
   const argv = getStringArgv(params)
@@ -38,12 +24,20 @@ export function remoteCliRequestTimeoutMs(params: Record<string, unknown>): numb
     return undefined
   }
   const commandPath = parseRemoteCommandPath(argv)
-  const timeoutFlag = findLastTimeoutMsFlag(argv)
+  const timeoutFlag = findLastTimeoutFlag(argv, 'timeout-ms')
+  if (commandPath[0] === 'terminal' && commandPath[1] === 'send') {
+    const waitFlag = findLastTimeoutFlag(argv, 'wait-submit')
+    const seconds =
+      waitFlag?.raw === undefined ? null : parsePositiveSafeIntegerNumericText(waitFlag.raw)
+    if (seconds !== null && seconds <= 3600) {
+      return Math.max(REMOTE_CLI_LONG_WAIT_BASE_MS, seconds * 1000 + REMOTE_CLI_LONG_WAIT_GRACE_MS)
+    }
+  }
   if (commandPath[0] === 'orchestration' && commandPath[1] === 'ask') {
     const parsed =
       timeoutFlag?.raw === undefined ? null : parsePositiveSafeIntegerText(timeoutFlag.raw)
     const effective = clampOrchestrationAskTimeoutMs(parsed ?? undefined)
-    return Math.max(ORCHESTRATION_ASK_RELAY_BASE_MS, effective + ORCHESTRATION_ASK_RELAY_GRACE_MS)
+    return Math.max(REMOTE_CLI_LONG_WAIT_BASE_MS, effective + REMOTE_CLI_LONG_WAIT_GRACE_MS)
   }
   const base = isWaitStyleCliRequest(argv, commandPath)
     ? REMOTE_CLI_WAIT_TIMEOUT_MS
@@ -69,15 +63,16 @@ function isWaitStyleCliRequest(argv: string[], commandPath: string[]): boolean {
   )
 }
 
-function findLastTimeoutMsFlag(argv: string[]): { raw: string | undefined } | null {
+function findLastTimeoutFlag(argv: string[], name: string): { raw: string | undefined } | null {
+  const flag = `--${name}`
   let result: { raw: string | undefined } | null = null
   for (let index = 0; index < argv.length; index += 1) {
     const token = argv[index]
-    if (token === '--timeout-ms') {
+    if (token === flag) {
       const next = argv[index + 1]
       result = { raw: next?.startsWith('--') ? undefined : next }
-    } else if (token.startsWith('--timeout-ms=')) {
-      result = { raw: token.slice('--timeout-ms='.length) }
+    } else if (token.startsWith(`${flag}=`)) {
+      result = { raw: token.slice(flag.length + 1) }
     }
   }
   return result
@@ -106,7 +101,7 @@ function parseRemoteCommandPath(argv: string[]): string[] {
     }
 
     const next = argv[index + 1]
-    if (!REMOTE_TIMEOUT_BOOLEAN_FLAGS.has(assignment) && next && !next.startsWith('--')) {
+    if (!CLI_BOOLEAN_FLAGS.has(assignment) && next && !next.startsWith('--')) {
       index += 1
     }
   }