feat(hooks): run boot.md on gateway startup

docs/cli/hooks.md

@@ -7,7 +7,7 @@ read_when:
 
 # `clawdbot hooks`
 
-Manage agent hooks (event-driven automations for commands like `/new`, `/reset`, etc.).
+Manage agent hooks (event-driven automations for commands like `/new`, `/reset`, and gateway startup).
 
 Related:
 - Hooks: [Hooks](/hooks)
@@ -29,9 +29,10 @@ List all discovered hooks from workspace, managed, and bundled directories.
 **Example output:**
 
 ```
-Hooks (3/3 ready)
+Hooks (4/4 ready)
 
 Ready:
+  🚀 boot-md ✓ - Run BOOT.md on gateway startup
   📝 command-logger ✓ - Log all command events to a centralized audit file
   💾 session-memory ✓ - Save session context to memory when /new command is issued
   😈 soul-evil ✓ - Swap injected SOUL content during a purge window or by random chance
@@ -107,8 +108,8 @@ Show summary of hook eligibility status (how many are ready vs. not ready).
 ```
 Hooks Status
 
-Total hooks: 2
+Total hooks: 4
-Ready: 2
+Ready: 4
 Not ready: 0
 ```
 
@@ -273,3 +274,17 @@ clawdbot hooks enable soul-evil
 ```
 
 **See:** [SOUL Evil Hook](/hooks/soul-evil)
+
+### boot-md
+
+Runs `BOOT.md` when the gateway starts (after channels start).
+
+**Events**: `gateway:startup`
+
+**Enable**:
+
+```bash
+clawdbot hooks enable boot-md
+```
+
+**See:** [boot-md documentation](/hooks#boot-md)

docs/concepts/agent-workspace.md

@@ -86,6 +86,10 @@ These are the standard files Clawdbot expects inside the workspace:
   - Optional tiny checklist for heartbeat runs.
   - Keep it short to avoid token burn.
 
+- `BOOT.md`
+  - Optional startup checklist executed on gateway restart when internal hooks are enabled.
+  - Keep it short; use the message tool for outbound sends.
+
 - `BOOTSTRAP.md`
   - One-time first-run ritual.
   - Only created for a brand-new workspace.

docs/docs.json

@@ -657,6 +657,10 @@
       "source": "/templates/AGENTS",
       "destination": "/reference/templates/AGENTS"
     },
+    {
+      "source": "/templates/BOOT",
+      "destination": "/reference/templates/BOOT"
+    },
     {
       "source": "/templates/BOOTSTRAP",
       "destination": "/reference/templates/BOOTSTRAP"
@@ -1051,6 +1055,7 @@
           "reference/RELEASING",
           "reference/AGENTS.default",
           "reference/templates/AGENTS",
+          "reference/templates/BOOT",
           "reference/templates/BOOTSTRAP",
           "reference/templates/HEARTBEAT",
           "reference/templates/IDENTITY",

docs/hooks.md

@@ -37,10 +37,11 @@ The hooks system allows you to:
 
 ### Bundled Hooks
 
-Clawdbot ships with three bundled hooks that are automatically discovered:
+Clawdbot ships with four bundled hooks that are automatically discovered:
 
 - **💾 session-memory**: Saves session context to your agent workspace (default `~/clawd/memory/`) when you issue `/new`
 - **📝 command-logger**: Logs all command events to `~/.clawdbot/logs/commands.log`
+- **🚀 boot-md**: Runs `BOOT.md` when the gateway starts (requires internal hooks enabled)
 - **😈 soul-evil**: Swaps injected `SOUL.md` content with `SOUL_EVIL.md` during a purge window or by random chance
 
 List available hooks:
@@ -195,7 +196,7 @@ Each event includes:
 
 ```typescript
 {
-  type: 'command' | 'session' | 'agent',
+  type: 'command' | 'session' | 'agent' | 'gateway',
   action: string,              // e.g., 'new', 'reset', 'stop'
   sessionKey: string,          // Session identifier
   timestamp: Date,             // When the event occurred
@@ -228,6 +229,12 @@ Triggered when agent commands are issued:
 
 - **`agent:bootstrap`**: Before workspace bootstrap files are injected (hooks may mutate `context.bootstrapFiles`)
 
+### Gateway Events
+
+Triggered when the gateway starts:
+
+- **`gateway:startup`**: After channels start and hooks are loaded
+
 ### Future Events
 
 Planned event types:
@@ -542,6 +549,26 @@ clawdbot hooks enable soul-evil
 }
 ```
 
+### boot-md
+
+Runs `BOOT.md` when the gateway starts (after channels start).
+Internal hooks must be enabled for this to run.
+
+**Events**: `gateway:startup`
+
+**Requirements**: `workspace.dir` must be configured
+
+**What it does**:
+1. Reads `BOOT.md` from your workspace
+2. Runs the instructions via the agent runner
+3. Sends any requested outbound messages via the message tool
+
+**Enable**:
+
+```bash
+clawdbot hooks enable boot-md
+```
+
 ## Best Practices
 
 ### Keep Handlers Fast
@@ -614,6 +641,7 @@ The gateway logs hook loading at startup:
 ```
 Registered hook: session-memory -> command:new
 Registered hook: command-logger -> command
+Registered hook: boot-md -> gateway:startup
 ```
 
 ### Check Discovery

docs/reference/templates/BOOT.md

@@ -0,0 +1,9 @@
+---
+summary: "Workspace template for BOOT.md"
+read_when:
+  - Adding a BOOT.md checklist
+---
+# BOOT.md
+
+Add short, explicit instructions for what Clawdbot should do on startup (enable `hooks.internal.enabled`).
+If the task sends a message, use the message tool and then reply with NO_REPLY.

src/gateway/boot.test.ts

@@ -0,0 +1,71 @@
+import fs from "node:fs/promises";
+import os from "node:os";
+import path from "node:path";
+
+import { beforeEach, describe, expect, it, vi } from "vitest";
+
+const agentCommand = vi.fn();
+
+vi.mock("../commands/agent.js", () => ({ agentCommand }));
+
+const { runBootOnce } = await import("./boot.js");
+const { resolveMainSessionKey } = await import("../config/sessions/main-session.js");
+
+describe("runBootOnce", () => {
+  beforeEach(() => {
+    vi.clearAllMocks();
+  });
+
+  const makeDeps = () => ({
+    sendMessageWhatsApp: vi.fn(),
+    sendMessageTelegram: vi.fn(),
+    sendMessageDiscord: vi.fn(),
+    sendMessageSlack: vi.fn(),
+    sendMessageSignal: vi.fn(),
+    sendMessageIMessage: vi.fn(),
+  });
+
+  it("skips when BOOT.md is missing", async () => {
+    const workspaceDir = await fs.mkdtemp(path.join(os.tmpdir(), "clawdbot-boot-"));
+    await expect(
+      runBootOnce({ cfg: {}, deps: makeDeps(), workspaceDir }),
+    ).resolves.toEqual({ status: "skipped", reason: "missing" });
+    expect(agentCommand).not.toHaveBeenCalled();
+    await fs.rm(workspaceDir, { recursive: true, force: true });
+  });
+
+  it("skips when BOOT.md is empty", async () => {
+    const workspaceDir = await fs.mkdtemp(path.join(os.tmpdir(), "clawdbot-boot-"));
+    await fs.writeFile(path.join(workspaceDir, "BOOT.md"), "   \n", "utf-8");
+    await expect(
+      runBootOnce({ cfg: {}, deps: makeDeps(), workspaceDir }),
+    ).resolves.toEqual({ status: "skipped", reason: "empty" });
+    expect(agentCommand).not.toHaveBeenCalled();
+    await fs.rm(workspaceDir, { recursive: true, force: true });
+  });
+
+  it("runs agent command when BOOT.md exists", async () => {
+    const workspaceDir = await fs.mkdtemp(path.join(os.tmpdir(), "clawdbot-boot-"));
+    const content = "Say hello when you wake up.";
+    await fs.writeFile(path.join(workspaceDir, "BOOT.md"), content, "utf-8");
+
+    agentCommand.mockResolvedValue(undefined);
+    await expect(
+      runBootOnce({ cfg: {}, deps: makeDeps(), workspaceDir }),
+    ).resolves.toEqual({ status: "ran" });
+
+    expect(agentCommand).toHaveBeenCalledTimes(1);
+    const call = agentCommand.mock.calls[0]?.[0];
+    expect(call).toEqual(
+      expect.objectContaining({
+        deliver: false,
+        sessionKey: resolveMainSessionKey({}),
+      }),
+    );
+    expect(call?.message).toContain("BOOT.md:");
+    expect(call?.message).toContain(content);
+    expect(call?.message).toContain("NO_REPLY");
+
+    await fs.rm(workspaceDir, { recursive: true, force: true });
+  });
+});

src/gateway/boot.ts

@@ -0,0 +1,92 @@
+import fs from "node:fs/promises";
+import path from "node:path";
+
+import { SILENT_REPLY_TOKEN } from "../auto-reply/tokens.js";
+import type { CliDeps } from "../cli/deps.js";
+import type { ClawdbotConfig } from "../config/config.js";
+import { resolveMainSessionKey } from "../config/sessions/main-session.js";
+import { agentCommand } from "../commands/agent.js";
+import { createSubsystemLogger } from "../logging.js";
+import { type RuntimeEnv, defaultRuntime } from "../runtime.js";
+
+const log = createSubsystemLogger("gateway/boot");
+const BOOT_FILENAME = "BOOT.md";
+
+export type BootRunResult =
+  | { status: "skipped"; reason: "missing" | "empty" }
+  | { status: "ran" }
+  | { status: "failed"; reason: string };
+
+function buildBootPrompt(content: string) {
+  return [
+    "You are running a boot check. Follow BOOT.md instructions exactly.",
+    "",
+    "BOOT.md:",
+    content,
+    "",
+    "If BOOT.md asks you to send a message, use the message tool (action=send with channel + target).",
+    "Use the `target` field (not `to`) for message tool destinations.",
+    `After sending with the message tool, reply with ONLY: ${SILENT_REPLY_TOKEN}.`,
+    `If nothing needs attention, reply with ONLY: ${SILENT_REPLY_TOKEN}.`,
+  ].join("\n");
+}
+
+async function loadBootFile(
+  workspaceDir: string,
+): Promise<{ content?: string; status: "ok" | "missing" | "empty" }> {
+  const bootPath = path.join(workspaceDir, BOOT_FILENAME);
+  try {
+    const content = await fs.readFile(bootPath, "utf-8");
+    const trimmed = content.trim();
+    if (!trimmed) return { status: "empty" };
+    return { status: "ok", content: trimmed };
+  } catch (err) {
+    const anyErr = err as { code?: string };
+    if (anyErr.code === "ENOENT") return { status: "missing" };
+    throw err;
+  }
+}
+
+export async function runBootOnce(params: {
+  cfg: ClawdbotConfig;
+  deps: CliDeps;
+  workspaceDir: string;
+}): Promise<BootRunResult> {
+  const bootRuntime: RuntimeEnv = {
+    log: () => {},
+    error: (message) => log.error(String(message)),
+    exit: defaultRuntime.exit,
+  };
+  let result: Awaited<ReturnType<typeof loadBootFile>>;
+  try {
+    result = await loadBootFile(params.workspaceDir);
+  } catch (err) {
+    const message = err instanceof Error ? err.message : String(err);
+    log.error(`boot: failed to read ${BOOT_FILENAME}: ${message}`);
+    return { status: "failed", reason: message };
+  }
+
+  if (result.status === "missing" || result.status === "empty") {
+    return { status: "skipped", reason: result.status };
+  }
+
+  const sessionKey = resolveMainSessionKey(params.cfg);
+  const message = buildBootPrompt(result.content ?? "");
+
+  try {
+    await agentCommand(
+      {
+        message,
+        sessionKey,
+        deliver: false,
+      },
+      bootRuntime,
+      params.deps,
+    );
+    return { status: "ran" };
+  } catch (err) {
+    const messageText = err instanceof Error ? err.message : String(err);
+    log.error(`boot: agent run failed: ${messageText}`);
+    return { status: "failed", reason: messageText };
+  }
+}

src/gateway/server-startup.ts

@@ -8,7 +8,11 @@ import {
 import type { CliDeps } from "../cli/deps.js";
 import type { loadConfig } from "../config/config.js";
 import { startGmailWatcher } from "../hooks/gmail-watcher.js";
-import { clearInternalHooks } from "../hooks/internal-hooks.js";
+import {
+  clearInternalHooks,
+  createInternalHookEvent,
+  triggerInternalHook,
+} from "../hooks/internal-hooks.js";
 import { loadInternalHooks } from "../hooks/loader.js";
 import type { loadClawdbotPlugins } from "../plugins/loader.js";
 import { type PluginServicesHandle, startPluginServices } from "../plugins/services.js";
@@ -122,6 +126,17 @@ export async function startGatewaySidecars(params: {
     );
   }
 
+  if (params.cfg.hooks?.internal?.enabled) {
+    setTimeout(() => {
+      const hookEvent = createInternalHookEvent("gateway", "startup", "gateway:startup", {
+        cfg: params.cfg,
+        deps: params.deps,
+        workspaceDir: params.defaultWorkspaceDir,
+      });
+      void triggerInternalHook(hookEvent);
+    }, 250);
+  }
+
   let pluginServices: PluginServicesHandle | null = null;
   try {
     pluginServices = await startPluginServices({

src/hooks/bundled/README.md

@@ -47,6 +47,20 @@ Swaps injected `SOUL.md` content with `SOUL_EVIL.md` during a purge window or by
 clawdbot hooks enable soul-evil
 ```
 
+### 🚀 boot-md
+
+Runs `BOOT.md` whenever the gateway starts (after channels start).
+
+**Events**: `gateway:startup`
+**What it does**: Executes BOOT.md instructions via the agent runner.
+**Output**: Whatever the instructions request (for example, outbound messages).
+
+**Enable**:
+
+```bash
+clawdbot hooks enable boot-md
+```
+
 ## Hook Structure
 
 Each hook is a directory containing:
@@ -156,6 +170,7 @@ Currently supported events:
 - **command:reset**: `/reset` command
 - **command:stop**: `/stop` command
 - **agent:bootstrap**: Before workspace bootstrap files are injected
+- **gateway:startup**: Gateway startup (after channels start)
 
 More event types coming soon (session lifecycle, agent errors, etc.).
 
@@ -165,7 +180,7 @@ Hook handlers receive an `InternalHookEvent` object:
 
 ```typescript
 interface InternalHookEvent {
-  type: "command" | "session" | "agent";
+  type: "command" | "session" | "agent" | "gateway";
   action: string; // e.g., 'new', 'reset', 'stop'
   sessionKey: string;
   context: Record<string, unknown>;

src/hooks/bundled/boot-md/HOOK.md

@@ -0,0 +1,19 @@
+---
+name: boot-md
+description: "Run BOOT.md on gateway startup"
+homepage: https://docs.clawd.bot/hooks#boot-md
+metadata:
+  {
+    "clawdbot":
+      {
+        "emoji": "🚀",
+        "events": ["gateway:startup"],
+        "requires": { "config": ["workspace.dir"] },
+        "install": [{ "id": "bundled", "kind": "bundled", "label": "Bundled with Clawdbot" }],
+      },
+  }
+---
+
+# Boot Checklist Hook
+
+Runs `BOOT.md` every time the gateway starts, if the file exists in the workspace.

src/hooks/bundled/boot-md/handler.ts

@@ -0,0 +1,27 @@
+import type { CliDeps } from "../../../cli/deps.js";
+import { createDefaultDeps } from "../../../cli/deps.js";
+import type { ClawdbotConfig } from "../../../config/config.js";
+import { runBootOnce } from "../../../gateway/boot.js";
+import type { HookHandler } from "../../hooks.js";
+
+type BootHookContext = {
+  cfg?: ClawdbotConfig;
+  workspaceDir?: string;
+  deps?: CliDeps;
+};
+
+const runBootChecklist: HookHandler = async (event) => {
+  if (event.type !== "gateway" || event.action !== "startup") {
+    return;
+  }
+
+  const context = (event.context ?? {}) as BootHookContext;
+  if (!context.cfg || !context.workspaceDir) {
+    return;
+  }
+
+  const deps = context.deps ?? createDefaultDeps();
+  await runBootOnce({ cfg: context.cfg, deps, workspaceDir: context.workspaceDir });
+};
+
+export default runBootChecklist;

src/hooks/internal-hooks.ts

@@ -8,7 +8,7 @@
 import type { WorkspaceBootstrapFile } from "../agents/workspace.js";
 import type { ClawdbotConfig } from "../config/config.js";
 
-export type InternalHookEventType = "command" | "session" | "agent";
+export type InternalHookEventType = "command" | "session" | "agent" | "gateway";
 
 export type AgentBootstrapHookContext = {
   workspaceDir: string;
@@ -26,7 +26,7 @@ export type AgentBootstrapHookEvent = InternalHookEvent & {
 };
 
 export interface InternalHookEvent {
-  /** The type of event (command, session, agent, etc.) */
+  /** The type of event (command, session, agent, gateway, etc.) */
   type: InternalHookEventType;
   /** The specific action within the type (e.g., 'new', 'reset', 'stop') */
   action: string;