diff --git a/apps/macos/Sources/Clawdis/GatewayLaunchAgentManager.swift b/apps/macos/Sources/Clawdis/GatewayLaunchAgentManager.swift
index 585b88a0c..e0a302088 100644
--- a/apps/macos/Sources/Clawdis/GatewayLaunchAgentManager.swift
+++ b/apps/macos/Sources/Clawdis/GatewayLaunchAgentManager.swift
@@ -10,6 +10,10 @@ enum GatewayLaunchAgentManager {
         "\(bundlePath)/Contents/Resources/Relay/clawdis-gateway"
     }
 
+    private static func relayDir(bundlePath: String) -> String {
+        "\(bundlePath)/Contents/Resources/Relay"
+    }
+
     static func status() async -> Bool {
         guard FileManager.default.fileExists(atPath: self.plistURL.path) else { return false }
         let result = await self.runLaunchctl(["print", "gui/\(getuid())/\(gatewayLaunchdLabel)"])
@@ -45,6 +49,10 @@ enum GatewayLaunchAgentManager {
 
     private static func writePlist(bundlePath: String, port: Int) {
         let gatewayBin = self.gatewayExecutablePath(bundlePath: bundlePath)
+        let relayDir = self.relayDir(bundlePath: bundlePath)
+        let preferredPath =
+            ([relayDir] + CommandResolver.preferredPaths())
+                .joined(separator: ":")
         let plist = """
         <?xml version="1.0" encoding="UTF-8"?>
         <!DOCTYPE plist PUBLIC "-//Apple//DTD PLIST 1.0//EN" "http://www.apple.com/DTDs/PropertyList-1.0.dtd">
@@ -69,7 +77,7 @@ enum GatewayLaunchAgentManager {
           <key>EnvironmentVariables</key>
           <dict>
             <key>PATH</key>
-            <string>\(CommandResolver.preferredPaths().joined(separator: ":"))</string>
+            <string>\(preferredPath)</string>
             <key>CLAWDIS_SKIP_BROWSER_CONTROL_SERVER</key>
             <string>1</string>
             <key>CLAWDIS_IMAGE_BACKEND</key>
diff --git a/src/gateway/server.ts b/src/gateway/server.ts
index 31dec3b75..3a21dfbf2 100644
--- a/src/gateway/server.ts
+++ b/src/gateway/server.ts
@@ -67,6 +67,7 @@ import {
   requestNodePairing,
   verifyNodeToken,
 } from "../infra/node-pairing.js";
+import { ensureClawdisCliOnPath } from "../infra/path-env.js";
 import { enqueueSystemEvent } from "../infra/system-events.js";
 import {
   listSystemPresence,
@@ -102,6 +103,8 @@ import { requestReplyHeartbeatNow } from "../web/reply-heartbeat-wake.js";
 import { buildMessageWithAttachments } from "./chat-attachments.js";
 import { handleControlUiHttpRequest } from "./control-ui.js";
 
+ensureClawdisCliOnPath();
+
 let stopBrowserControlServerIfStarted: (() => Promise<void>) | null = null;
 
 async function startBrowserControlServerIfEnabled(): Promise<void> {
diff --git a/src/index.ts b/src/index.ts
index 3b7ad6362..24df05eac 100644
--- a/src/index.ts
+++ b/src/index.ts
@@ -17,6 +17,7 @@ import {
   saveSessionStore,
 } from "./config/sessions.js";
 import { ensureBinary } from "./infra/binaries.js";
+import { ensureClawdisCliOnPath } from "./infra/path-env.js";
 import {
   describePortOwner,
   ensurePortAvailable,
@@ -30,6 +31,7 @@ import { monitorWebProvider } from "./provider-web.js";
 import { assertProvider, normalizeE164, toWhatsappJid } from "./utils.js";
 
 dotenv.config({ quiet: true });
+ensureClawdisCliOnPath();
 
 // Capture all console output into structured logs while keeping stdout/stderr behavior.
 enableConsoleCapture();
diff --git a/src/infra/path-env.test.ts b/src/infra/path-env.test.ts
new file mode 100644
index 000000000..b3dbf969f
--- /dev/null
+++ b/src/infra/path-env.test.ts
@@ -0,0 +1,66 @@
+import fs from "node:fs/promises";
+import os from "node:os";
+import path from "node:path";
+
+import { describe, expect, it } from "vitest";
+
+import { ensureClawdisCliOnPath } from "./path-env.js";
+
+describe("ensureClawdisCliOnPath", () => {
+  it("prepends the bundled Relay dir when a sibling clawdis exists", async () => {
+    const tmp = await fs.mkdtemp(path.join(os.tmpdir(), "clawdis-path-"));
+    try {
+      const relayDir = path.join(tmp, "Relay");
+      await fs.mkdir(relayDir, { recursive: true });
+      const gatewayPath = path.join(relayDir, "clawdis-gateway");
+      const cliPath = path.join(relayDir, "clawdis");
+      await fs.writeFile(gatewayPath, "#!/bin/sh\nexit 0\n", "utf-8");
+      await fs.writeFile(cliPath, "#!/bin/sh\necho ok\n", "utf-8");
+      await fs.chmod(gatewayPath, 0o755);
+      await fs.chmod(cliPath, 0o755);
+
+      const originalPath = process.env.PATH;
+      const originalFlag = process.env.CLAWDIS_PATH_BOOTSTRAPPED;
+      process.env.PATH = "/usr/bin";
+      delete process.env.CLAWDIS_PATH_BOOTSTRAPPED;
+      try {
+        ensureClawdisCliOnPath({
+          execPath: gatewayPath,
+          cwd: tmp,
+          homeDir: tmp,
+          platform: "darwin",
+        });
+        const updated = process.env.PATH ?? "";
+        expect(updated.split(path.delimiter)[0]).toBe(relayDir);
+      } finally {
+        process.env.PATH = originalPath;
+        if (originalFlag === undefined)
+          delete process.env.CLAWDIS_PATH_BOOTSTRAPPED;
+        else process.env.CLAWDIS_PATH_BOOTSTRAPPED = originalFlag;
+      }
+    } finally {
+      await fs.rm(tmp, { recursive: true, force: true });
+    }
+  });
+
+  it("is idempotent", () => {
+    const originalPath = process.env.PATH;
+    const originalFlag = process.env.CLAWDIS_PATH_BOOTSTRAPPED;
+    process.env.PATH = "/bin";
+    process.env.CLAWDIS_PATH_BOOTSTRAPPED = "1";
+    try {
+      ensureClawdisCliOnPath({
+        execPath: "/tmp/does-not-matter",
+        cwd: "/tmp",
+        homeDir: "/tmp",
+        platform: "darwin",
+      });
+      expect(process.env.PATH).toBe("/bin");
+    } finally {
+      process.env.PATH = originalPath;
+      if (originalFlag === undefined)
+        delete process.env.CLAWDIS_PATH_BOOTSTRAPPED;
+      else process.env.CLAWDIS_PATH_BOOTSTRAPPED = originalFlag;
+    }
+  });
+});
diff --git a/src/infra/path-env.ts b/src/infra/path-env.ts
new file mode 100644
index 000000000..f8703eba0
--- /dev/null
+++ b/src/infra/path-env.ts
@@ -0,0 +1,99 @@
+import fs from "node:fs";
+import os from "node:os";
+import path from "node:path";
+
+type EnsureClawdisPathOpts = {
+  execPath?: string;
+  cwd?: string;
+  homeDir?: string;
+  platform?: NodeJS.Platform;
+  pathEnv?: string;
+};
+
+function isExecutable(filePath: string): boolean {
+  try {
+    fs.accessSync(filePath, fs.constants.X_OK);
+    return true;
+  } catch {
+    return false;
+  }
+}
+
+function isDirectory(dirPath: string): boolean {
+  try {
+    return fs.statSync(dirPath).isDirectory();
+  } catch {
+    return false;
+  }
+}
+
+function mergePath(params: { existing: string; prepend: string[] }): string {
+  const partsExisting = params.existing
+    .split(path.delimiter)
+    .map((part) => part.trim())
+    .filter(Boolean);
+  const partsPrepend = params.prepend
+    .map((part) => part.trim())
+    .filter(Boolean);
+
+  const seen = new Set<string>();
+  const merged: string[] = [];
+  for (const part of [...partsPrepend, ...partsExisting]) {
+    if (!seen.has(part)) {
+      seen.add(part);
+      merged.push(part);
+    }
+  }
+  return merged.join(path.delimiter);
+}
+
+function candidateBinDirs(opts: EnsureClawdisPathOpts): string[] {
+  const execPath = opts.execPath ?? process.execPath;
+  const cwd = opts.cwd ?? process.cwd();
+  const homeDir = opts.homeDir ?? os.homedir();
+  const platform = opts.platform ?? process.platform;
+
+  const candidates: string[] = [];
+
+  // Bun bundled (macOS app): `clawdis` is shipped next to `clawdis-gateway`.
+  try {
+    const execDir = path.dirname(execPath);
+    const siblingClawdis = path.join(execDir, "clawdis");
+    if (isExecutable(siblingClawdis)) candidates.push(execDir);
+  } catch {
+    // ignore
+  }
+
+  // Project-local installs (best effort): if a `node_modules/.bin/clawdis` exists near cwd,
+  // include it. This helps when running under launchd or other minimal PATH environments.
+  const localBinDir = path.join(cwd, "node_modules", ".bin");
+  if (isExecutable(path.join(localBinDir, "clawdis")))
+    candidates.push(localBinDir);
+
+  // Common global install locations (macOS first).
+  if (platform === "darwin") {
+    candidates.push(path.join(homeDir, "Library", "pnpm"));
+  }
+  candidates.push(path.join(homeDir, ".local", "share", "pnpm"));
+  candidates.push(path.join(homeDir, ".bun", "bin"));
+  candidates.push(path.join(homeDir, ".yarn", "bin"));
+  candidates.push("/opt/homebrew/bin", "/usr/local/bin", "/usr/bin", "/bin");
+
+  return candidates.filter(isDirectory);
+}
+
+/**
+ * Best-effort PATH bootstrap so skills that require the `clawdis` CLI can run
+ * under launchd/minimal environments (and inside the macOS bun bundle).
+ */
+export function ensureClawdisCliOnPath(opts: EnsureClawdisPathOpts = {}) {
+  if (process.env.CLAWDIS_PATH_BOOTSTRAPPED === "1") return;
+  process.env.CLAWDIS_PATH_BOOTSTRAPPED = "1";
+
+  const existing = opts.pathEnv ?? process.env.PATH ?? "";
+  const prepend = candidateBinDirs(opts);
+  if (prepend.length === 0) return;
+
+  const merged = mergePath({ existing, prepend });
+  if (merged) process.env.PATH = merged;
+}