kimaki 0.26.0 → 0.28.0

package/src/system-message.ts

@@ -13,6 +13,7 @@ import fs from 'node:fs'
 import path from 'node:path'
 import { getDataDir } from './config.js'
 import { store } from './store.js'
+import { SESSION_SEARCH_DEFAULT_DAYS } from './session-search.js'
 
 /** Subfolder under the kimaki data dir for session system prompt side-channel files. */
 export const SESSION_SYSTEM_PROMPT_DIR = 'session-system'
@@ -175,7 +176,7 @@ this feature by restarting kimaki with the \`--no-critique\` flag.
 const KIMAKI_TUNNEL_INSTRUCTIONS = `
 ## running dev servers with tunnel access
 
-ALWAYS use \`kimaki tunnel\` when starting any dev server. NEVER run \`pnpm dev\`, \`npm run dev\`, or any dev server command without wrapping it in \`kimaki tunnel\`. Always invoke Kimaki directly as \`kimaki\`, never via \`npx\` or \`bunx\`. The user is on Discord, not at the terminal — localhost URLs are useless to them. They need a tunnel URL to access the site.
+When starting a local dev server that the Discord user should open in a browser, prefer wrapping it in \`kimaki tunnel\` so they get a public URL. Localhost URLs are useless from Discord. Invoke Kimaki directly as \`kimaki\`, not via \`npx\` or \`bunx\`.
 
 Use \`bunx tuistory\` to run the tunnel + dev server combo in the background so it persists across commands. This is preferable to raw shell backgrounding because you can wait for real output, read logs, and interact with the running process.
 
@@ -316,9 +317,13 @@ export type ThreadStartMarker = {
   /**
    * OpenCode session ID of the parent session that spawned this thread via
    * `kimaki send --parent-session`. Exposed in the child system message so the
-   * child can message the parent only when the user explicitly asks.
-   */
+    * child can message the parent only when the user explicitly asks.
+    */
   parentSessionId?: string
+  /** Wake prompt posted after kimaki_sleep. Ingress must not cancel this sleep. */
+  sleepWake?: boolean
+  /** delivery_id of the session_sleeps row this wake delivers. */
+  sleepId?: string
 }
 
 export function isInjectedPromptMarker({
@@ -337,6 +342,40 @@ export type AgentInfo = {
   description?: string
 }
 
+/**
+ * Info about the scheduled task that started this session, resolved once per
+ * session and kept stable across turns so the system prompt prefix stays
+ * cacheable.
+ */
+export type ScheduledTaskSystemContext = {
+  /** Scheduled task ID. Missing for one-shot 'at' tasks (deleted after run). */
+  taskId?: number
+  scheduleKind: 'at' | 'cron'
+  /** Cron expression in the task's timezone. Only set for 'cron' tasks. */
+  cronExpr?: string | null
+  /** IANA timezone the cron fires in. Defaults to UTC when unset. */
+  timezone?: string | null
+}
+
+function getScheduledTaskSection(context: ScheduledTaskSystemContext): string {
+  const origin = context.taskId
+    ? `kimaki scheduled task #${context.taskId}`
+    : 'a one-time kimaki scheduled task'
+  const schedule = context.scheduleKind === 'cron' && context.cronExpr
+    ? `Schedule: cron \`${context.cronExpr}\`${context.timezone ? ` in ${context.timezone}` : ' in UTC'}.`
+    : context.scheduleKind === 'at'
+      ? 'This task runs once and does not repeat.'
+      : ''
+  return `
+## scheduled task session
+
+This session was started automatically by ${origin}.
+${schedule}
+When your run is done, just stop: the task fires again on its schedule and starts a fresh session automatically.
+Do NOT use \`kimaki_sleep\` to wait for the next run. Sleeping pins this session and never triggers the next one; each firing of the task starts a new session on its own.
+`
+}
+
 function escapePromptAttribute(value: string): string {
   return value
     .replaceAll('&', '&')
@@ -357,6 +396,7 @@ export function getOpencodePromptContext({
   userId,
   sourceMessageId,
   sourceThreadId,
+  threadName,
   repliedMessage,
   worktree,
   currentAgent,
@@ -366,6 +406,7 @@ export function getOpencodePromptContext({
   userId?: string
   sourceMessageId?: string
   sourceThreadId?: string
+  threadName?: string
   repliedMessage?: RepliedMessageContext
   worktree?: WorktreeInfo
   currentAgent?: string
@@ -384,6 +425,9 @@ export function getOpencodePromptContext({
     ...(sourceThreadId
       ? [` thread-id="${escapePromptAttribute(sourceThreadId)}"`]
       : []),
+    ...(threadName
+      ? [` thread-name="${escapePromptAttribute(threadName)}"`]
+      : []),
   ].join('')
   const repliedMessageXml = repliedMessage
     ? `This message was a reply to message
@@ -422,6 +466,7 @@ export function getOpencodeSystemMessage({
   agents,
   userId,
   parentSessionId,
+  scheduledTask,
 }: {
   sessionId: string
   channelId?: string
@@ -440,6 +485,11 @@ export function getOpencodeSystemMessage({
    * per-parent block. Never auto-derive this from OpenCode parent session IDs.
    */
   parentSessionId?: string
+  /**
+   * Set only when the session was started by a scheduled task. Resolved from
+   * the session_start_sources row, so it stays identical across turns.
+   */
+  scheduledTask?: ScheduledTaskSystemContext
 }) {
   const userArg = ` --user '${userId || '<discord-user-id>'}'`
   const parentSessionArg = ` --parent-session ${sessionId}`
@@ -465,6 +515,12 @@ export function getOpencodeSystemMessage({
   return `
 The user is reading your messages from inside Discord, via kimaki.dev
 
+## Discord output
+
+Be concise. Do not narrate between tool calls. Discord posts every text part, so commentary like "I'll read the file" or "now I'll run tests" is noise.
+Do not output text until you are ready to give the user the final answer for this turn. Tool calls can run with no preceding text.
+Exceptions: when a tool requires user-visible text first (\`question\`, \`kimaki_action_buttons\`, \`kimaki_file_upload\`, \`kimaki_sleep\`), write that required text, then call the tool.
+
 ## bash tool
 
 When calling the bash tool, always include these extra fields alongside \`command\`:
@@ -481,12 +537,12 @@ interface BashToolInput {
 }
 \`\`\`
 
-\`description\` is shown to the user in Discord as a summary of the bash call.
+\`description\` is shown in Discord when the bash command is longer than 50 characters.
 \`hasSideEffect\` distinguishes essential bash calls from read-only ones in low-verbosity mode.
 
 Your current OpenCode session ID is: ${sessionId}${channelId ? `\nYour current Discord channel ID is: ${channelId}` : ''}${threadId ? `\nYour current Discord thread ID is: ${threadId}` : ''}${guildId ? `\nYour current Discord guild ID is: ${guildId}` : ''}${parentSessionContext}
 
-Per-turn Discord metadata like the current user and current agent is delivered in synthetic user message parts.
+Per-turn Discord metadata like the current user, current agent, and Discord thread title is delivered in synthetic user message parts.
 
 ## permissions
 
@@ -509,6 +565,7 @@ Do not restart the bot unless the user explicitly asks for it.
 
 ## debugging kimaki issues
 
+ALWAYS read https://kimaki.dev/docs/guides/report-bugs first before submitting any issue to Kimaki. That page is the source of truth for exporting session jsonl, sharing evidence in a gist, and filing bugs. Never open a pull request on remorses/kimaki unless remorses asked for one in a comment on the issue.
 If there are internal kimaki issues (sessions not responding, bot errors, unexpected behavior), read the log file at \`${getDataDir()}/kimaki.log\`. This file contains detailed logs of all bot activity including session creation, event handling, errors, and API calls. The log file is reset every time the bot restarts, so it only contains logs from the current run.
 
 ## uploading files to discord
@@ -517,6 +574,8 @@ To upload files to the Discord thread (images, screenshots, long files that woul
 
 kimaki upload-to-discord --session ${sessionId} <file1> [file2] ...
 
+NEVER show images with markdown like \`![alt](/tmp/file.png)\` or \`![alt](file://...)\`. Discord does not render local markdown images. ALWAYS upload them with \`kimaki upload-to-discord\` so they appear as real Discord attachments. Do this for every screenshot, generated image, and visual step the user should see.
+
 ## generating audio from text
 
 When the user asks you to generate audio of some text so they can listen instead of reading, use \`kimaki tts\` to create a speech file and \`kimaki upload-to-discord\` to send it to the thread. Only use this when the user explicitly asks for audio.
@@ -538,9 +597,18 @@ see --help for options like voice, speed, etc.
 To ask the user to upload files from their device, use \`kimaki_file_upload\`. This shows a native file picker dialog in Discord. The files are downloaded to the project's \`uploads/\` directory and the tool returns the local file paths.
 You MUST call \`kimaki_file_upload\` LAST, after ALL text.
 
+## sleeping the session
+
+Use \`kimaki_sleep\` to pause this session for hours or days, then continue when the time is reached. The sleep is stored in SQLite and survives bot restarts.
+Pass either \`duration\` (\`30s\`, \`2h\`, \`1d\`) or \`until\` (UTC ISO ending with \`Z\`, example \`2026-08-20T09:00:00Z\`).
+You MUST call \`kimaki_sleep\` LAST, after ALL text. Do not call more tools after it.
+A new user message cancels the sleep. If you still need to wake later after answering, call \`kimaki_sleep\` again with \`until\` set to the original UTC time.
+The tool result is not a wake. After it succeeds, write one short line that you are waiting, then stop. Do not continue the wait reason and do not pretend time has passed.
+Wake is a later Discord message that starts with \`Woke after sleeping until\`. Only then continue the wait reason.
+${scheduledTask ? getScheduledTaskSection(scheduledTask) : ''}
 ## archiving the current thread
 
-To archive the current Discord thread (hide it from sidebar) and stop the session, run:
+To archive the current Discord thread (hide it from sidebar) without stopping the session, run:
 
 kimaki session archive ${archiveTarget}
 
@@ -555,6 +623,17 @@ kimaki session abort <session_id>
 This stops the AI from processing but keeps the thread visible in Discord.
 Different from \`kimaki session archive\` which hides the thread.
 
+## updating the session title
+
+When the session scope or goal changed from the first message, update the title:
+
+kimaki session title 'Short title' --session ${sessionId}
+
+The current Discord thread title is in the per-turn \`<discord-user thread-name="..." />\` metadata.
+This updates the OpenCode title. Discord follows automatically.
+Do not retitle every turn. Discord rate-limits thread renames.
+Keep titles short. Do not add emoji. Do not copy ⬦, btw:, or Fork: prefixes.
+
 ## discord user mentions
 
 Prefer Discord user IDs for mentions. Discord bots cannot ping by @name; use \`<@userId>\` in message text or pass the ID to \`--user\`.
@@ -653,13 +732,13 @@ kimaki send --thread <thread_id> --prompt '/<agentname>-agent' --agent <current_
 Use \`--send-at\` to schedule a one-time or recurring task:
 
 kimaki send --channel ${channelId} --prompt 'Reminder: review open PRs' --send-at '2026-03-01T09:00:00Z' --agent <current_agent>${parentSessionArg}${userArg}
-kimaki send --channel ${channelId} --prompt 'Run weekly test suite and summarize failures' --send-at '0 9 * * 1' --agent <current_agent>${parentSessionArg}${userArg}
+kimaki send --channel ${channelId} --prompt 'Run weekly test suite and summarize failures' --send-at '0 9 * * 1' --agent <current_agent>${parentSessionArg}
 
 Use \`--pre-run '<command>'\` to check whether a scheduled task should start. Kimaki runs the command in the project directory. Exit code 0 starts the session and appends stdout to the prompt. Any other exit code skips that occurrence. Command output is written to the Kimaki log.
 
 Scheduled tasks do not overlap by default. Add \`--allow-concurrency\` only when concurrent sessions from the same task are safe.
 
-**ALWAYS pass \`--user\` when scheduling a task.** Discord only shows a thread in the left sidebar to its members. Without \`--user\`, kimaki does not ensure anyone is a member, so the task can fire completely unnoticed if the user never joined the thread or already left it. This applies to \`--channel\` and \`--thread\` scheduling alike.
+Pass \`--user\` when the user should see or act on the thread. Omit \`--user\` for routine autonomous work (digests, monitors, housekeeping) so the thread does not appear in the user's Discord sidebar. Discord only shows a thread in the left sidebar to its members. Without \`--user\`, kimaki does not ensure anyone is a member. This applies to \`--channel\` and \`--thread\` scheduling alike.
 
 ALL scheduling is in UTC. Dates must be UTC ISO format ending with \`Z\`. Cron expressions also fire in UTC (e.g. \`0 9 * * 1\` means 9:00 UTC every Monday).
 When the user specifies a time without a timezone, ask them to confirm their timezone or the UTC equivalent. Never guess the user's timezone.
@@ -671,14 +750,14 @@ When the user specifies a time without a timezone, ask them to confirm their tim
 - \`--pre-run\` to start only when a project command exits with code 0
 - \`--allow-concurrency\` to permit overlapping runs from the same task
 - \`--parent-session\` to pass this session as parent of the scheduled child
-- \`--user\` to add a specific user to the scheduled thread (always pass this)
+- \`--user\` to add a specific user to the scheduled thread. Omit this for quiet autonomous work
 
 \`--wait\` is incompatible with \`--send-at\` because scheduled tasks run in the future.
 
 Keep scheduled task prompts **short**. The prompt text becomes the first message in the Discord thread, so long prompts clutter the channel. Instead of inlining the full task description in \`--prompt\`, write a markdown file in the project's \`tasks/\` folder and reference it:
 
 \`\`\`bash
-kimaki send --channel ${channelId} --prompt 'Read tasks/weekly-test-suite.md and follow instructions' --send-at '0 9 * * 1' --agent <current_agent>${parentSessionArg}${userArg}
+kimaki send --channel ${channelId} --prompt 'Read tasks/weekly-test-suite.md and follow instructions' --send-at '0 9 * * 1' --agent <current_agent>${parentSessionArg}
 \`\`\`
 
 The task file should contain all the detail: goal, constraints, expected output, completion criteria. Use this frontmatter format:
@@ -697,7 +776,7 @@ For simple reminders and notifications (\`--notify-only\`), inline the prompt di
 Notification strategy:
 - NEVER use \`@username\` (e.g. \`@Tommy\`) directly in task prompts. The prompt text becomes the first message in the thread, so a raw \`@\` mention triggers an actual Discord ping every time the task fires. Instead, wrap it in inline code like \`\\\`@Tommy\\\`\`, or use Discord user ID mentions like \`<@USER_ID>\` only in the body of the prompt where the agent will process it, not in the opening line.
 - If a task needs user attention, add "mention the user via Discord user ID when task requires user review" in the task md file.
-- With \`--user\`, the user is added to the thread and receives thread-level notifications.
+- With \`--user\`, the user is added to the thread and receives thread-level notifications. Omit \`--user\` when the work should stay out of the sidebar.
 - If a scheduled task completes with no actionable result, archive the session: \`kimaki session archive ${archiveTarget}\`
 
 Manage scheduled tasks with:
@@ -706,7 +785,7 @@ kimaki task list
 kimaki task edit <id> --prompt "new prompt" [--send-at "new schedule"] [--pre-run "command"] [--allow-concurrency true|false] [--user "<discord-user-id>"] [--model "provider/model"] [--agent "<agent>"]
 kimaki task delete <id>
 
-\`kimaki task list\` prints \`userId\`, \`agent\`, and \`model\` columns. A \`-\` in \`userId\` means nobody is added to the thread when that task fires, so the user may never see it. Fix it with \`kimaki task edit <id> --user '<discord-user-id>'\` instead of deleting and recreating the task. Change model or agent in place with \`--model\` / \`--agent\` (empty string clears the override). Do not read SQLite or recreate the task just to swap model.
+\`kimaki task list\` prints \`userId\`, \`agent\`, and \`model\` columns. A \`-\` in \`userId\` means nobody is added to the thread when that task fires, so the user may never see it. Add a user with \`kimaki task edit <id> --user '<discord-user-id>'\`. Clear a stored user with \`kimaki task edit <id> --user ''\`. Change model or agent in place with \`--model\` / \`--agent\` (empty string clears the override). Do not read SQLite or recreate the task just to swap model.
 
 \`kimaki session list\` also shows if a session was started by a scheduled \`delay\` or \`cron\` task, including task ID when available.
 
@@ -784,15 +863,22 @@ To list all sessions in this project (shows which were started via kimaki):
 kimaki session list
 kimaki session list --json  # machine-readable output
 kimaki session list --project /path/to/project  # specific project
+
+# List only in-progress sessions. Exit status is 1 when none remain.
+kimaki session list --active
 \`\`\`
 
-To search past sessions for this project (supports plain text or /regex/flags):
+Titles prefixed with \`btw:\` are side sessions that answer a related user question in parallel. They are not duplicate sessions of the main task.
+
+To search past sessions (supports plain text or /regex/flags). Defaults to this project and the last ${SESSION_SEARCH_DEFAULT_DAYS} days. Use \`--days 0\` for all time. Use \`--all\` to search every locally registered project:
 
 \`\`\`bash
 kimaki session search "auth timeout"
+kimaki session search "auth timeout" --days 0
 kimaki session search "/error\\s+42/i"
 kimaki session search "rate limit" --project /path/to/project
 kimaki session search "/panic|crash/i" --channel <channel_id>
+kimaki session search "auth timeout" --all
 \`\`\`
 
 To read a session's full conversation as markdown, pipe to a file and grep it to avoid wasting context.
@@ -804,6 +890,29 @@ kimaki session read <sessionId> > ./tmp/session.md 2>/dev/null
 
 Then use grep/read tools on the file to find what you need.
 
+### who edited a file
+
+To find the session that last edited a file, run:
+
+\`\`\`bash
+kimaki session editors src/foo.ts
+kimaki session editors src/foo.ts --json
+\`\`\`
+
+Output is newest first. Each row has:
+
+- **session ID** (\`ses_xxx\`)
+- **title** (Discord thread name, so you can tell what that session was doing)
+- **time ago** (when that session last edited the file)
+
+Use this before a commit when this session did not edit the file. Put the original session ID as the last line of the commit message:
+
+\`\`\`
+Session: ses_xxx
+\`\`\`
+
+If this session edited the file, use this session ID instead. If several files come from different sessions, split the commit by session. Do not attribute another session's edits to this one.
+
 ## cross-project commands
 
 When the user references another project by name, run \`kimaki project list\` to find its directory path and channel ID. Then read files, search code, or run commands directly in that directory. If the project is not listed, use \`kimaki project add /path/to/repo\` to register it and create a Discord channel for it. Do not add subfolders of an existing project — only add root project directories.
@@ -870,7 +979,7 @@ Use \`--wait\` to block until a session completes and print its full conversatio
 
 When the user asks you to wait for an existing session, run \`kimaki session wait <session_id>\` yourself via Bash, then continue from the printed session markdown. Do not tell the user to run the command.
 
-IMPORTANT: if you run \`kimaki send --wait\` or \`kimaki session wait <session_id>\` via the Bash tool, you must set the Bash tool \`timeout\` to **20 minutes or more** (example: \`timeout: 1_500_000\`). Otherwise the tool will terminate early (default is 2 minutes) and you won't see long sessions.
+IMPORTANT: if you run \`kimaki send --wait\`, \`kimaki session wait <session_id>\`, or the active-session wait loop via the Bash tool, you must set the Bash tool \`timeout\` to **20 minutes or more** (example: \`timeout: 1_500_000\`). Otherwise the tool will terminate early (default is 2 minutes) and you won't see long sessions.
 
 If your Bash tool timeout triggers anyway, fall back to reading the session output from disk:
 
@@ -885,9 +994,14 @@ kimaki send --thread <thread_id> --prompt 'Run the tests' --wait --agent <curren
 
 # Wait for a session that was already started elsewhere
 kimaki session wait <session_id>
+
+# Wait until every other in-progress session in this project finishes
+while kimaki session list --active --exclude ${sessionId}; do sleep 5; done
 \`\`\`
 
-The command exits with the session markdown on stdout once the model finishes responding.
+\`session list --active\` exits with status 0 while it finds active sessions and status 1 when none remain. Exclude the current session in a wait loop so the loop does not wait for itself.
+
+\`session wait\` exits with the session markdown on stdout once the model finishes responding.
 
 Use \`--wait\` when you need to:
 - **Fix a bug in another project** before continuing here (e.g. fix a dependency, then resume)
@@ -1001,7 +1115,7 @@ You MUST write ALL user-visible text FIRST.
 You MUST call \`question\` LAST, after ALL text parts.
 NEVER call \`question\` before your text. Discord will hide the message.
 
-The same rule applies to \`kimaki_action_buttons\` and \`kimaki_file_upload\`.
+The same rule applies to \`kimaki_action_buttons\`, \`kimaki_file_upload\`, and \`kimaki_sleep\`.
 You MUST call them LAST, after ALL text.
 
 ALWAYS use \`question\` when you ask the user a question. Do not write a numbered list in plain text.

package/src/task-runner.ts

@@ -1,6 +1,6 @@
-// Scheduled task runner for executing due `send --send-at` jobs in the bot process.
+// Scheduled task runner for due `send --send-at` jobs and session sleep wakes.
 
-import { type REST, Routes } from 'discord.js'
+import { DiscordAPIError, type REST, Routes } from 'discord.js'
 import { createDiscordRest } from './discord-urls.js'
 import { ensureThreadMember } from './discord-utils.js'
 import YAML from 'yaml'
@@ -20,8 +20,14 @@ import {
   releaseScheduledTaskClaim,
   setScheduledTaskRunThread,
   type ScheduledTask,
+  type SessionSleep,
+  claimSessionSleepAttempt,
+  getDueSessionSleeps,
+  getThreadIdBySessionId,
+  markSessionSleepFailed,
 } from './database.js'
 import { execAsync } from './exec-async.js'
+import { QUEUE_PREFIX } from './message-formatting.js'
 import { initializeOpencodeForDirectory } from './opencode.js'
 import { createLogger, formatErrorWithStack, LogPrefix } from './logger.js'
 import { notifyError } from './sentry.js'
@@ -29,6 +35,7 @@ import type { ThreadStartMarker } from './system-message.js'
 import {
   type ScheduledTaskPayload,
   appendTaskCommandOutput,
+  formatSessionSleepWakePrompt,
   getNextCronRun,
   getPromptPreview,
   parseScheduledTaskPayload,
@@ -93,7 +100,7 @@ async function executeThreadScheduledTask({
   const embed = [{ color: 0x2b2d31, footer: { text: YAML.stringify(marker) } }]
   // Newline between prefix and prompt so leading /command detection can
   // find the command on its own line.
-  const prefixedPrompt = `» **kimaki-cli:**\n${prompt}`
+  const prefixedPrompt = `${QUEUE_PREFIX}**kimaki-cli:**\n${prompt}`
 
   // Re-join the user before posting, so the message they get notified about is
   // in a thread they are already a member of. Works on archived threads too;
@@ -129,6 +136,132 @@ async function executeThreadScheduledTask({
   return payload.threadId
 }
 
+/** Wait before retrying a wake that ingress has not consumed yet. */
+const SLEEP_WAKE_RETRY_AFTER_MS = 30_000
+const SLEEP_WAKE_MAX_ATTEMPTS = 5
+
+type SleepWakeFailure = { error: Error; permanent: boolean }
+
+export function buildSessionSleepWakeBody({
+  deliveryId,
+  wakeAt,
+  reason,
+}: {
+  deliveryId: string
+  wakeAt: Date
+  reason: string | null
+}) {
+  const marker: ThreadStartMarker = {
+    start: true,
+    sleepWake: true,
+    sleepId: deliveryId,
+  }
+  return {
+    content: formatSessionSleepWakePrompt({ wakeAt, reason }),
+    embeds: [{ color: 0x2b2d31, footer: { text: YAML.stringify(marker) } }],
+    // Discord limits nonces to 25 characters. The full ID stays in the marker.
+    // A stable nonce deduplicates retries when a successful response is lost.
+    nonce: deliveryId.replaceAll('-', '').slice(0, 25),
+    enforce_nonce: true,
+  }
+}
+
+async function postSessionSleepWake({
+  rest,
+  sleep,
+  threadId,
+}: {
+  rest: REST
+  sleep: SessionSleep
+  threadId: string
+}): Promise<SleepWakeFailure | null> {
+  // `.then(() => null)` keeps the success type concrete. Returning the raw post
+  // value would widen the union to `unknown` and erase the failure shape.
+  return await rest
+    .post(Routes.channelMessages(threadId), {
+      body: buildSessionSleepWakeBody({
+        deliveryId: sleep.delivery_id,
+        wakeAt: sleep.wake_at,
+        reason: sleep.reason,
+      }),
+    })
+    .then((): SleepWakeFailure | null => {
+      return null
+    })
+    .catch((error): SleepWakeFailure => {
+      // Only an unknown channel/message is genuinely unrecoverable. A 403 is
+      // often temporary (permissions revoked, thread locked) so it keeps
+      // retrying until the attempt budget runs out.
+      const permanent =
+        error instanceof DiscordAPIError &&
+        error.status === 404
+      return {
+        error: new Error(
+          `Failed to post sleep wake for session ${sleep.session_id}`,
+          { cause: error },
+        ),
+        permanent,
+      }
+    })
+}
+
+export async function wakeDueSessionSleeps({
+  rest,
+  now = new Date(),
+  limit = 20,
+}: {
+  rest: REST
+  now?: Date
+  limit?: number
+}): Promise<void> {
+  const dueSleeps = await getDueSessionSleeps({
+    now,
+    retryAfterMs: SLEEP_WAKE_RETRY_AFTER_MS,
+    limit,
+  })
+  for (const sleep of dueSleeps) {
+    // Reserves an attempt but stays `planned`. The row only leaves `planned`
+    // when ingress consumes the wake, so dying anywhere below costs one retry
+    // delay instead of losing the wake.
+    const claimed = await claimSessionSleepAttempt({
+      sessionId: sleep.session_id,
+      deliveryId: sleep.delivery_id,
+      now,
+      retryAfterMs: SLEEP_WAKE_RETRY_AFTER_MS,
+    })
+    if (!claimed) continue
+
+    // Resolved now, not when the tool ran, so a session rebound by /resume
+    // wakes in the thread that currently owns it.
+    const threadId = await getThreadIdBySessionId(claimed.session_id)
+    if (!threadId) {
+      await markSessionSleepFailed({
+        sessionId: claimed.session_id,
+        deliveryId: claimed.delivery_id,
+      })
+      taskLogger.warn(
+        `[task-runner] no thread owns session ${claimed.session_id}, dropping sleep wake`,
+      )
+      continue
+    }
+
+    // A successful post changes nothing here on purpose: ingress owns the
+    // transition out of `planned` when the wake actually becomes a turn.
+    const postResult = await postSessionSleepWake({ rest, sleep: claimed, threadId })
+    if (!postResult) continue
+
+    const exhausted = claimed.attempts >= SLEEP_WAKE_MAX_ATTEMPTS
+    if (postResult.permanent || exhausted) {
+      await markSessionSleepFailed({
+        sessionId: claimed.session_id,
+        deliveryId: claimed.delivery_id,
+      })
+    }
+    taskLogger.error(`[task-runner] ${formatErrorWithStack(postResult.error)}`)
+    void notifyError(postResult.error, 'Session sleep wake failed')
+  }
+}
+
 async function executeChannelScheduledTask({
   rest,
   task,
@@ -564,6 +697,8 @@ async function runTaskRunnerTick({
     await previous
     await processDueTask({ rest, task })
   }, Promise.resolve())
+
+  await wakeDueSessionSleeps({ rest })
 }
 
 export function startTaskRunner({