diff --git a/cli/package-lock.json b/cli/package-lock.json
index 4936a55..ffb5694 100644
--- a/cli/package-lock.json
+++ b/cli/package-lock.json
@@ -19,22 +19,510 @@
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+      "resolved": "https://registry.npmjs.org/rolldown/-/rolldown-1.0.0-rc.11.tgz",
+      "integrity": "sha512-NRjoKMusSjfRbSYiH3VSumlkgFe7kYAa3pzVOsVYVFY3zb5d7nS+a3KGQ7hJKXuYWbzJKPVQ9Wxq2UvyK+ENpw==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "@oxc-project/types": "=0.122.0",
+        "@rolldown/pluginutils": "1.0.0-rc.11"
+      },
+      "bin": {
+        "rolldown": "bin/cli.mjs"
+      },
+      "engines": {
+        "node": "^20.19.0 || >=22.12.0"
+      },
+      "optionalDependencies": {
+        "@rolldown/binding-android-arm64": "1.0.0-rc.11",
+        "@rolldown/binding-darwin-arm64": "1.0.0-rc.11",
+        "@rolldown/binding-darwin-x64": "1.0.0-rc.11",
+        "@rolldown/binding-freebsd-x64": "1.0.0-rc.11",
+        "@rolldown/binding-linux-arm-gnueabihf": "1.0.0-rc.11",
+        "@rolldown/binding-linux-arm64-gnu": "1.0.0-rc.11",
+        "@rolldown/binding-linux-arm64-musl": "1.0.0-rc.11",
+        "@rolldown/binding-linux-ppc64-gnu": "1.0.0-rc.11",
+        "@rolldown/binding-linux-s390x-gnu": "1.0.0-rc.11",
+        "@rolldown/binding-linux-x64-gnu": "1.0.0-rc.11",
+        "@rolldown/binding-linux-x64-musl": "1.0.0-rc.11",
+        "@rolldown/binding-openharmony-arm64": "1.0.0-rc.11",
+        "@rolldown/binding-wasm32-wasi": "1.0.0-rc.11",
+        "@rolldown/binding-win32-arm64-msvc": "1.0.0-rc.11",
+        "@rolldown/binding-win32-x64-msvc": "1.0.0-rc.11"
+      }
+    },
+    "node_modules/siginfo": {
+      "version": "2.0.0",
+      "resolved": "https://registry.npmjs.org/siginfo/-/siginfo-2.0.0.tgz",
+      "integrity": "sha512-ybx0WO1/8bSBLEWXZvEd7gMW3Sn3JFlW3TvX1nREbDLRNQNaeNN8WK0meBwPdAaOI7TtRRRJn/Es1zhrrCHu7g==",
+      "dev": true,
+      "license": "ISC"
+    },
+    "node_modules/source-map-js": {
+      "version": "1.2.1",
+      "resolved": "https://registry.npmjs.org/source-map-js/-/source-map-js-1.2.1.tgz",
+      "integrity": "sha512-UXWMKhLOwVKb728IUtQPXxfYU+usdybtUrK/8uGE8CQMvrhOpwvzDBwj0QhSL7MQc7vIsISBG8VQ8+IDQxpfQA==",
+      "dev": true,
+      "license": "BSD-3-Clause",
+      "engines": {
+        "node": ">=0.10.0"
+      }
+    },
+    "node_modules/stackback": {
+      "version": "0.0.2",
+      "resolved": "https://registry.npmjs.org/stackback/-/stackback-0.0.2.tgz",
+      "integrity": "sha512-1XMJE5fQo1jGH6Y/7ebnwPOBEkIEnT4QF32d5R1+VXdXveM0IBMJt8zfaxX1P3QhVwrYe+576+jkANtSS2mBbw==",
+      "dev": true,
+      "license": "MIT"
+    },
+    "node_modules/std-env": {
+      "version": "4.0.0",
+      "resolved": "https://registry.npmjs.org/std-env/-/std-env-4.0.0.tgz",
+      "integrity": "sha512-zUMPtQ/HBY3/50VbpkupYHbRroTRZJPRLvreamgErJVys0ceuzMkD44J/QjqhHjOzK42GQ3QZIeFG1OYfOtKqQ==",
+      "dev": true,
+      "license": "MIT"
+    },
     "node_modules/supports-color": {
       "version": "7.2.0",
       "resolved": "https://registry.npmjs.org/supports-color/-/supports-color-7.2.0.tgz",
@@ -288,6 +1249,82 @@
         "node": ">=8"
       }
     },
+    "node_modules/tinybench": {
+      "version": "2.9.0",
+      "resolved": "https://registry.npmjs.org/tinybench/-/tinybench-2.9.0.tgz",
+      "integrity": "sha512-0+DUvqWMValLmha6lr4kD8iAMK1HzV0/aKnCtWb9v9641TnP/MFb7Pc2bxoxQjTXAErryXVgUOfv2YqNllqGeg==",
+      "dev": true,
+      "license": "MIT"
+    },
+    "node_modules/tinyexec": {
+      "version": "1.0.4",
+      "resolved": "https://registry.npmjs.org/tinyexec/-/tinyexec-1.0.4.tgz",
+      "integrity": "sha512-u9r3uZC0bdpGOXtlxUIdwf9pkmvhqJdrVCH9fapQtgy/OeTTMZ1nqH7agtvEfmGui6e1XxjcdrlxvxJvc3sMqw==",
+      "dev": true,
+      "license": "MIT",
+      "engines": {
+        "node": ">=18"
+      }
+    },
+    "node_modules/tinyglobby": {
+      "version": "0.2.15",
+      "resolved": "https://registry.npmjs.org/tinyglobby/-/tinyglobby-0.2.15.tgz",
+      "integrity": "sha512-j2Zq4NyQYG5XMST4cbs02Ak8iJUdxRM0XI5QyxXuZOzKOINmWurp3smXu3y5wDcJrptwpSjgXHzIQxR0omXljQ==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "fdir": "^6.5.0",
+        "picomatch": "^4.0.3"
+      },
+      "engines": {
+        "node": ">=12.0.0"
+      },
+      "funding": {
+        "url": "https://github.com/sponsors/SuperchupuDev"
+      }
+    },
+    "node_modules/tinyglobby/node_modules/fdir": {
+      "version": "6.5.0",
+      "resolved": "https://registry.npmjs.org/fdir/-/fdir-6.5.0.tgz",
+      "integrity": "sha512-tIbYtZbucOs0BRGqPJkshJUYdL+SDH7dVM8gjy+ERp3WAUjLEFJE+02kanyHtwjWOnwrKYBiwAmM0p4kLJAnXg==",
+      "dev": true,
+      "license": "MIT",
+      "engines": {
+        "node": ">=12.0.0"
+      },
+      "peerDependencies": {
+        "picomatch": "^3 || ^4"
+      },
+      "peerDependenciesMeta": {
+        "picomatch": {
+          "optional": true
+        }
+      }
+    },
+    "node_modules/tinyglobby/node_modules/picomatch": {
+      "version": "4.0.4",
+      "resolved": "https://registry.npmjs.org/picomatch/-/picomatch-4.0.4.tgz",
+      "integrity": "sha512-QP88BAKvMam/3NxH6vj2o21R6MjxZUAd6nlwAS/pnGvN9IVLocLHxGYIzFhg6fUQ+5th6P4dv4eW9jX3DSIj7A==",
+      "dev": true,
+      "license": "MIT",
+      "peer": true,
+      "engines": {
+        "node": ">=12"
+      },
+      "funding": {
+        "url": "https://github.com/sponsors/jonschlinkert"
+      }
+    },
+    "node_modules/tinyrainbow": {
+      "version": "3.1.0",
+      "resolved": "https://registry.npmjs.org/tinyrainbow/-/tinyrainbow-3.1.0.tgz",
+      "integrity": "sha512-Bf+ILmBgretUrdJxzXM0SgXLZ3XfiaUuOj/IKQHuTXip+05Xn+uyEYdVg0kYDipTBcLrCVyUzAPz7QmArb0mmw==",
+      "dev": true,
+      "license": "MIT",
+      "engines": {
+        "node": ">=14.0.0"
+      }
+    },
     "node_modules/to-regex-range": {
       "version": "5.0.1",
       "resolved": "https://registry.npmjs.org/to-regex-range/-/to-regex-range-5.0.1.tgz",
@@ -300,6 +1337,14 @@
         "node": ">=8.0"
       }
     },
+    "node_modules/tslib": {
+      "version": "2.8.1",
+      "resolved": "https://registry.npmjs.org/tslib/-/tslib-2.8.1.tgz",
+      "integrity": "sha512-oJFu94HQb+KVduSUQL7wnpmqnfmLsOA/nAh6b6EH0wCEoK0/mPeXU6c3wKDV83MkOuHPRHtSXKKU99IBazS/2w==",
+      "dev": true,
+      "license": "0BSD",
+      "optional": true
+    },
     "node_modules/typescript": {
       "version": "5.9.3",
       "resolved": "https://registry.npmjs.org/typescript/-/typescript-5.9.3.tgz",
@@ -320,6 +1365,209 @@
       "integrity": "sha512-iwDZqg0QAGrg9Rav5H4n0M64c3mkR59cJ6wQp+7C4nI0gsmExaedaYLNO44eT4AtBBwjbTiGPMlt2Md0T9H9JQ==",
       "dev": true,
       "license": "MIT"
+    },
+    "node_modules/vite": {
+      "version": "8.0.2",
+      "resolved": "https://registry.npmjs.org/vite/-/vite-8.0.2.tgz",
+      "integrity": "sha512-1gFhNi+bHhRE/qKZOJXACm6tX4bA3Isy9KuKF15AgSRuRazNBOJfdDemPBU16/mpMxApDPrWvZ08DcLPEoRnuA==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "lightningcss": "^1.32.0",
+        "picomatch": "^4.0.3",
+        "postcss": "^8.5.8",
+        "rolldown": "1.0.0-rc.11",
+        "tinyglobby": "^0.2.15"
+      },
+      "bin": {
+        "vite": "bin/vite.js"
+      },
+      "engines": {
+        "node": "^20.19.0 || >=22.12.0"
+      },
+      "funding": {
+        "url": "https://github.com/vitejs/vite?sponsor=1"
+      },
+      "optionalDependencies": {
+        "fsevents": "~2.3.3"
+      },
+      "peerDependencies": {
+        "@types/node": "^20.19.0 || >=22.12.0",
+        "@vitejs/devtools": "^0.1.0",
+        "esbuild": "^0.27.0",
+        "jiti": ">=1.21.0",
+        "less": "^4.0.0",
+        "sass": "^1.70.0",
+        "sass-embedded": "^1.70.0",
+        "stylus": ">=0.54.8",
+        "sugarss": "^5.0.0",
+        "terser": "^5.16.0",
+        "tsx": "^4.8.1",
+        "yaml": "^2.4.2"
+      },
+      "peerDependenciesMeta": {
+        "@types/node": {
+          "optional": true
+        },
+        "@vitejs/devtools": {
+          "optional": true
+        },
+        "esbuild": {
+          "optional": true
+        },
+        "jiti": {
+          "optional": true
+        },
+        "less": {
+          "optional": true
+        },
+        "sass": {
+          "optional": true
+        },
+        "sass-embedded": {
+          "optional": true
+        },
+        "stylus": {
+          "optional": true
+        },
+        "sugarss": {
+          "optional": true
+        },
+        "terser": {
+          "optional": true
+        },
+        "tsx": {
+          "optional": true
+        },
+        "yaml": {
+          "optional": true
+        }
+      }
+    },
+    "node_modules/vite/node_modules/picomatch": {
+      "version": "4.0.4",
+      "resolved": "https://registry.npmjs.org/picomatch/-/picomatch-4.0.4.tgz",
+      "integrity": "sha512-QP88BAKvMam/3NxH6vj2o21R6MjxZUAd6nlwAS/pnGvN9IVLocLHxGYIzFhg6fUQ+5th6P4dv4eW9jX3DSIj7A==",
+      "dev": true,
+      "license": "MIT",
+      "engines": {
+        "node": ">=12"
+      },
+      "funding": {
+        "url": "https://github.com/sponsors/jonschlinkert"
+      }
+    },
+    "node_modules/vitest": {
+      "version": "4.1.1",
+      "resolved": "https://registry.npmjs.org/vitest/-/vitest-4.1.1.tgz",
+      "integrity": "sha512-yF+o4POL41rpAzj5KVILUxm1GCjKnELvaqmU9TLLUbMfDzuN0UpUR9uaDs+mCtjPe+uYPksXDRLQGGPvj1cTmA==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "@vitest/expect": "4.1.1",
+        "@vitest/mocker": "4.1.1",
+        "@vitest/pretty-format": "4.1.1",
+        "@vitest/runner": "4.1.1",
+        "@vitest/snapshot": "4.1.1",
+        "@vitest/spy": "4.1.1",
+        "@vitest/utils": "4.1.1",
+        "es-module-lexer": "^2.0.0",
+        "expect-type": "^1.3.0",
+        "magic-string": "^0.30.21",
+        "obug": "^2.1.1",
+        "pathe": "^2.0.3",
+        "picomatch": "^4.0.3",
+        "std-env": "^4.0.0-rc.1",
+        "tinybench": "^2.9.0",
+        "tinyexec": "^1.0.2",
+        "tinyglobby": "^0.2.15",
+        "tinyrainbow": "^3.0.3",
+        "vite": "^6.0.0 || ^7.0.0 || ^8.0.0",
+        "why-is-node-running": "^2.3.0"
+      },
+      "bin": {
+        "vitest": "vitest.mjs"
+      },
+      "engines": {
+        "node": "^20.0.0 || ^22.0.0 || >=24.0.0"
+      },
+      "funding": {
+        "url": "https://opencollective.com/vitest"
+      },
+      "peerDependencies": {
+        "@edge-runtime/vm": "*",
+        "@opentelemetry/api": "^1.9.0",
+        "@types/node": "^20.0.0 || ^22.0.0 || >=24.0.0",
+        "@vitest/browser-playwright": "4.1.1",
+        "@vitest/browser-preview": "4.1.1",
+        "@vitest/browser-webdriverio": "4.1.1",
+        "@vitest/ui": "4.1.1",
+        "happy-dom": "*",
+        "jsdom": "*",
+        "vite": "^6.0.0 || ^7.0.0 || ^8.0.0"
+      },
+      "peerDependenciesMeta": {
+        "@edge-runtime/vm": {
+          "optional": true
+        },
+        "@opentelemetry/api": {
+          "optional": true
+        },
+        "@types/node": {
+          "optional": true
+        },
+        "@vitest/browser-playwright": {
+          "optional": true
+        },
+        "@vitest/browser-preview": {
+          "optional": true
+        },
+        "@vitest/browser-webdriverio": {
+          "optional": true
+        },
+        "@vitest/ui": {
+          "optional": true
+        },
+        "happy-dom": {
+          "optional": true
+        },
+        "jsdom": {
+          "optional": true
+        },
+        "vite": {
+          "optional": false
+        }
+      }
+    },
+    "node_modules/vitest/node_modules/picomatch": {
+      "version": "4.0.4",
+      "resolved": "https://registry.npmjs.org/picomatch/-/picomatch-4.0.4.tgz",
+      "integrity": "sha512-QP88BAKvMam/3NxH6vj2o21R6MjxZUAd6nlwAS/pnGvN9IVLocLHxGYIzFhg6fUQ+5th6P4dv4eW9jX3DSIj7A==",
+      "dev": true,
+      "license": "MIT",
+      "engines": {
+        "node": ">=12"
+      },
+      "funding": {
+        "url": "https://github.com/sponsors/jonschlinkert"
+      }
+    },
+    "node_modules/why-is-node-running": {
+      "version": "2.3.0",
+      "resolved": "https://registry.npmjs.org/why-is-node-running/-/why-is-node-running-2.3.0.tgz",
+      "integrity": "sha512-hUrmaWBdVDcxvYqnyh09zunKzROWjbZTiNy8dBEjkS7ehEDQibXJ7XvlmtbwuTclUiIyN+CyXQD4Vmko8fNm8w==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "siginfo": "^2.0.0",
+        "stackback": "0.0.2"
+      },
+      "bin": {
+        "why-is-node-running": "cli.js"
+      },
+      "engines": {
+        "node": ">=8"
+      }
     }
   }
 }
diff --git a/cli/package.json b/cli/package.json
index d5f57a3..1ee8d9c 100644
--- a/cli/package.json
+++ b/cli/package.json
@@ -43,7 +43,9 @@
     "dev": "tsc --watch",
     "start": "node dist/cli.js",
     "prepack": "npm run build",
-    "postinstall": "echo 'ClaWatch installed successfully (pure WASM — no native build needed)'"
+    "postinstall": "echo 'ClaWatch installed successfully (pure WASM \u2014 no native build needed)'",
+    "test": "vitest run",
+    "test:watch": "vitest"
   },
   "dependencies": {
     "chalk": "^4.1.2",
@@ -52,6 +54,7 @@
   },
   "devDependencies": {
     "@types/node": "^20.14.0",
-    "typescript": "^5.5.0"
+    "typescript": "^5.5.0",
+    "vitest": "^4.1.1"
   }
-}
+}
\ No newline at end of file
diff --git a/cli/src/__tests__/update.test.ts b/cli/src/__tests__/update.test.ts
new file mode 100644
index 0000000..5b17d33
--- /dev/null
+++ b/cli/src/__tests__/update.test.ts
@@ -0,0 +1,262 @@
+import { describe, it, expect, vi } from "vitest";
+import { compareVersions, detectPackageManager, checkForUpdate } from "../update";
+
+// ─── compareVersions ───
+
+describe("compareVersions", () => {
+  it("returns up-to-date for identical versions", () => {
+    expect(compareVersions("1.2.2", "1.2.2")).toBe("up-to-date");
+  });
+
+  it("detects patch update available", () => {
+    expect(compareVersions("1.2.2", "1.2.3")).toBe("update-available");
+  });
+
+  it("detects minor update available", () => {
+    expect(compareVersions("1.2.2", "1.3.0")).toBe("update-available");
+  });
+
+  it("detects major update available", () => {
+    expect(compareVersions("1.2.2", "2.0.0")).toBe("update-available");
+  });
+
+  it("detects current is ahead (patch)", () => {
+    expect(compareVersions("1.2.3", "1.2.2")).toBe("ahead");
+  });
+
+  it("detects current is ahead (minor)", () => {
+    expect(compareVersions("1.3.0", "1.2.9")).toBe("ahead");
+  });
+
+  it("detects current is ahead (major)", () => {
+    expect(compareVersions("2.0.0", "1.9.9")).toBe("ahead");
+  });
+
+  it("handles v-prefix on current version", () => {
+    expect(compareVersions("v1.2.2", "1.2.3")).toBe("update-available");
+  });
+
+  it("handles v-prefix on latest version", () => {
+    expect(compareVersions("1.2.2", "v1.2.3")).toBe("update-available");
+  });
+
+  it("handles v-prefix on both versions", () => {
+    expect(compareVersions("v1.2.2", "v1.2.2")).toBe("up-to-date");
+  });
+
+  it("handles 0.x versions", () => {
+    expect(compareVersions("0.1.0", "0.2.0")).toBe("update-available");
+    expect(compareVersions("0.0.1", "0.0.2")).toBe("update-available");
+  });
+
+  it("handles single-segment versions gracefully", () => {
+    expect(compareVersions("1", "2")).toBe("update-available");
+    expect(compareVersions("2", "1")).toBe("ahead");
+  });
+
+  it("handles two-segment versions", () => {
+    expect(compareVersions("1.2", "1.3")).toBe("update-available");
+  });
+
+  it("handles non-numeric segments as 0", () => {
+    expect(compareVersions("1.beta.0", "1.0.1")).toBe("update-available");
+  });
+});
+
+// ─── detectPackageManager ───
+
+describe("detectPackageManager", () => {
+  it("detects npm when global module exists in lib/node_modules", () => {
+    const result = detectPackageManager({
+      execSync: (cmd) => {
+        if (cmd.includes("npm prefix -g")) return "/usr/local";
+        throw new Error("unexpected");
+      },
+      existsSync: (p) => p === "/usr/local/lib/node_modules/clawatch",
+    });
+    expect(result).toEqual({ manager: "npm", command: "npm update -g clawatch" });
+  });
+
+  it("detects npm on Windows-style path (no /lib)", () => {
+    const result = detectPackageManager({
+      execSync: (cmd) => {
+        if (cmd.includes("npm prefix -g")) return "C:\\Users\\me\\AppData\\Roaming\\npm";
+        throw new Error("unexpected");
+      },
+      existsSync: (p) => {
+        // Windows path join uses backslash
+        return p.includes("node_modules") && p.includes("clawatch") && !p.includes("lib");
+      },
+    });
+    expect(result).toEqual({ manager: "npm", command: "npm update -g clawatch" });
+  });
+
+  it("detects yarn when yarn global dir has clawatch", () => {
+    const result = detectPackageManager({
+      execSync: (cmd) => {
+        if (cmd.includes("npm prefix -g")) return "/usr/local";
+        if (cmd.includes("yarn global dir")) return "/home/user/.config/yarn/global";
+        throw new Error("unexpected");
+      },
+      existsSync: (p) => {
+        if (p.includes("yarn") && p.includes("node_modules/clawatch")) return true;
+        return false;
+      },
+    });
+    expect(result).toEqual({ manager: "yarn", command: "yarn global upgrade clawatch" });
+  });
+
+  it("detects pnpm when pnpm root has clawatch", () => {
+    const result = detectPackageManager({
+      execSync: (cmd) => {
+        if (cmd.includes("npm prefix -g")) return "/usr/local";
+        if (cmd.includes("yarn global dir")) throw new Error("not found");
+        if (cmd.includes("pnpm root -g")) return "/usr/local/lib/node_modules";
+        throw new Error("unexpected");
+      },
+      existsSync: (p) => {
+        if (p === "/usr/local/lib/node_modules/clawatch") return true;
+        return false;
+      },
+    });
+    // npm check passes first since path exists — but it's under /lib/node_modules
+    // Need to ensure npm doesn't match first for pnpm test
+    const pnpmResult = detectPackageManager({
+      execSync: (cmd) => {
+        if (cmd.includes("npm prefix -g")) return "/usr/local";
+        if (cmd.includes("yarn global dir")) throw new Error("not found");
+        if (cmd.includes("pnpm root -g")) return "/home/user/.pnpm-global";
+        throw new Error("unexpected");
+      },
+      existsSync: (p) => {
+        if (p === "/home/user/.pnpm-global/clawatch") return true;
+        return false;
+      },
+    });
+    expect(pnpmResult).toEqual({ manager: "pnpm", command: "pnpm update -g clawatch" });
+  });
+
+  it("falls back to npm install when npm exists but no global module found", () => {
+    const result = detectPackageManager({
+      execSync: (cmd) => {
+        if (cmd.includes("npm prefix -g")) return "/usr/local";
+        if (cmd.includes("yarn global dir")) throw new Error("not found");
+        if (cmd.includes("pnpm root -g")) throw new Error("not found");
+        if (cmd.includes("npm --version")) return "10.8.0";
+        throw new Error("unexpected");
+      },
+      existsSync: () => false,
+    });
+    expect(result).toEqual({ manager: "npm", command: "npm install -g clawatch@latest" });
+  });
+
+  it("returns null when no package manager is available", () => {
+    const result = detectPackageManager({
+      execSync: () => {
+        throw new Error("not found");
+      },
+      existsSync: () => false,
+    });
+    expect(result).toBeNull();
+  });
+
+  it("prioritizes npm over yarn and pnpm", () => {
+    // If npm global module exists, should pick npm even if yarn/pnpm also have it
+    const result = detectPackageManager({
+      execSync: (cmd) => {
+        if (cmd.includes("npm prefix -g")) return "/usr/local";
+        if (cmd.includes("yarn global dir")) return "/home/user/.yarn";
+        if (cmd.includes("pnpm root -g")) return "/home/user/.pnpm";
+        return "";
+      },
+      existsSync: () => true, // everything exists
+    });
+    expect(result?.manager).toBe("npm");
+  });
+
+  it("handles empty npm prefix gracefully", () => {
+    const result = detectPackageManager({
+      execSync: (cmd) => {
+        if (cmd.includes("npm prefix -g")) return "";
+        if (cmd.includes("yarn global dir")) throw new Error("no");
+        if (cmd.includes("pnpm root -g")) throw new Error("no");
+        if (cmd.includes("npm --version")) return "10.0.0";
+        throw new Error("no");
+      },
+      existsSync: () => false,
+    });
+    // Should fall through to npm fallback
+    expect(result).toEqual({ manager: "npm", command: "npm install -g clawatch@latest" });
+  });
+});
+
+// ─── checkForUpdate ───
+
+describe("checkForUpdate", () => {
+  it("returns up-to-date when versions match", () => {
+    const result = checkForUpdate({
+      currentVersion: "1.2.2",
+      latestVersion: "1.2.2",
+      checkOnly: false,
+    });
+    expect(result.action).toBe("up-to-date");
+  });
+
+  it("returns up-to-date when current is ahead", () => {
+    const result = checkForUpdate({
+      currentVersion: "2.0.0",
+      latestVersion: "1.9.9",
+      checkOnly: false,
+    });
+    expect(result.action).toBe("up-to-date");
+  });
+
+  it("returns check-only when update available but --check flag set", () => {
+    const result = checkForUpdate({
+      currentVersion: "1.2.2",
+      latestVersion: "1.3.0",
+      checkOnly: true,
+    });
+    expect(result.action).toBe("check-only");
+    expect(result.latestVersion).toBe("1.3.0");
+  });
+
+  it("returns update-available when update exists and no --check flag", () => {
+    const result = checkForUpdate({
+      currentVersion: "1.2.2",
+      latestVersion: "1.3.0",
+      checkOnly: false,
+    });
+    expect(result.action).toBe("update-available");
+    expect(result.currentVersion).toBe("1.2.2");
+    expect(result.latestVersion).toBe("1.3.0");
+  });
+
+  it("returns no-version when latest version is null", () => {
+    const result = checkForUpdate({
+      currentVersion: "1.2.2",
+      latestVersion: null,
+      checkOnly: false,
+    });
+    expect(result.action).toBe("no-version");
+  });
+
+  it("returns no-version when latest version is empty string treated as null", () => {
+    const result = checkForUpdate({
+      currentVersion: "1.2.2",
+      latestVersion: null,
+      checkOnly: true,
+    });
+    expect(result.action).toBe("no-version");
+  });
+
+  it("preserves version strings in result", () => {
+    const result = checkForUpdate({
+      currentVersion: "1.0.0",
+      latestVersion: "2.0.0",
+      checkOnly: false,
+    });
+    expect(result.currentVersion).toBe("1.0.0");
+    expect(result.latestVersion).toBe("2.0.0");
+  });
+});
diff --git a/cli/src/cli.ts b/cli/src/cli.ts
index 89307e2..090f564 100644
--- a/cli/src/cli.ts
+++ b/cli/src/cli.ts
@@ -8,6 +8,7 @@ import * as os from 'os';
 import { fork, spawn, ChildProcess } from 'child_process';
 import { loadConfig, saveConfig, configExists, paths, ensureDir, ClaWatchConfig, savePids, loadPids, clearPids, ManagedPids } from './config';
 import { execSync } from 'child_process';
+import { compareVersions, detectPackageManager, checkForUpdate } from './update';
 
 import * as net from 'net';
 
@@ -599,4 +600,96 @@ program
     }
   });
 
+// --- Update command ---
+program
+  .command('update')
+  .description('Check for updates and upgrade clawatch to the latest version')
+  .option('--check', 'Only check for updates without installing')
+  .action(async (opts) => {
+    const currentVersion = pkg.version;
+    console.log(chalk.bold('\n🔄 ClaWatch Update\n'));
+    console.log(`  Current version: ${chalk.cyan(currentVersion)}`);
+
+    // 1. Fetch latest version from npm registry
+    console.log(chalk.gray('  Checking npm registry...'));
+    let latestVersion: string;
+    try {
+      latestVersion = execSync('npm view clawatch version 2>/dev/null', { encoding: 'utf-8' }).trim();
+    } catch {
+      console.log(chalk.red('\n  ❌ Could not reach npm registry.'));
+      console.log(chalk.yellow('     Check your internet connection and try again.\n'));
+      process.exit(1);
+    }
+
+    if (!latestVersion) {
+      console.log(chalk.red('\n  ❌ Could not determine latest version.\n'));
+      process.exit(1);
+    }
+
+    console.log(`  Latest version:  ${chalk.cyan(latestVersion)}`);
+
+    // 2. Check update status using extracted logic
+    const updateCheck = checkForUpdate({
+      currentVersion,
+      latestVersion,
+      checkOnly: !!opts.check,
+    });
+
+    if (updateCheck.action === 'up-to-date') {
+      console.log(chalk.green('\n  ✅ Already on the latest version!\n'));
+      process.exit(0);
+    }
+
+    console.log(chalk.yellow(`\n  ⬆️  Update available: ${currentVersion} → ${latestVersion}`));
+
+    if (updateCheck.action === 'check-only') {
+      console.log(chalk.gray('  Run "clawatch update" (without --check) to install.\n'));
+      process.exit(0);
+    }
+
+    // 3. Detect package manager using extracted logic
+    const pm = detectPackageManager({
+      execSync: (cmd) => execSync(cmd, { encoding: 'utf-8' }),
+      existsSync: (p) => fs.existsSync(p),
+    });
+
+    if (!pm) {
+      console.log(chalk.red('\n  ❌ Could not detect package manager (npm, yarn, or pnpm).'));
+      console.log(chalk.yellow('     Install one first: https://nodejs.org\n'));
+      process.exit(1);
+    }
+
+    // 5. Prompt user (unless stdin is not a TTY)
+    const readline = require('readline');
+    if (process.stdin.isTTY) {
+      const rl = readline.createInterface({ input: process.stdin, output: process.stdout });
+      const answer = await new Promise<string>((resolve) => {
+        rl.question(chalk.white(`\n  Update via ${pm.manager}? [Y/n] `), (a: string) => {
+          rl.close();
+          resolve(a.trim().toLowerCase());
+        });
+      });
+
+      if (answer && answer !== 'y' && answer !== 'yes') {
+        console.log(chalk.yellow('\n  Update cancelled.\n'));
+        process.exit(0);
+      }
+    }
+
+    // 6. Run update
+    console.log(chalk.blue(`\n  Running: ${pm.command}\n`));
+    try {
+      execSync(pm.command, { stdio: 'inherit' });
+      console.log(chalk.green.bold(`\n  ✅ Updated to ${latestVersion}!`));
+      console.log(chalk.gray('     Restart ClaWatch to use the new version.\n'));
+    } catch (err) {
+      console.log(chalk.red(`\n  ❌ Update failed. Try manually: ${pm.command}`));
+      if (pm.manager === 'npm') {
+        console.log(chalk.yellow('     You may need: sudo npm install -g clawatch@latest'));
+      }
+      console.log('');
+      process.exit(1);
+    }
+  });
+
 program.parse();
diff --git a/cli/src/update.ts b/cli/src/update.ts
new file mode 100644
index 0000000..e24ffee
--- /dev/null
+++ b/cli/src/update.ts
@@ -0,0 +1,140 @@
+import * as fs from 'fs';
+import * as path from 'path';
+
+/**
+ * Compare two semver version strings.
+ * Returns: "up-to-date" | "update-available" | "ahead"
+ */
+export function compareVersions(
+  current: string,
+  latest: string
+): "up-to-date" | "update-available" | "ahead" {
+  if (current === latest) return "up-to-date";
+
+  const parseSemver = (v: string) => {
+    const cleaned = v.replace(/^v/, "");
+    const parts = cleaned.split(".").map((p) => parseInt(p, 10) || 0);
+    return { major: parts[0] || 0, minor: parts[1] || 0, patch: parts[2] || 0 };
+  };
+
+  const c = parseSemver(current);
+  const l = parseSemver(latest);
+
+  if (l.major > c.major) return "update-available";
+  if (l.major < c.major) return "ahead";
+  if (l.minor > c.minor) return "update-available";
+  if (l.minor < c.minor) return "ahead";
+  if (l.patch > c.patch) return "update-available";
+  if (l.patch < c.patch) return "ahead";
+
+  return "up-to-date";
+}
+
+export interface PackageManagerInfo {
+  manager: "npm" | "yarn" | "pnpm";
+  command: string;
+}
+
+/**
+ * Detect which package manager installed clawatch globally.
+ * Uses dependency injection for testability.
+ */
+export function detectPackageManager(opts: {
+  execSync: (cmd: string) => string;
+  existsSync: (p: string) => boolean;
+}): PackageManagerInfo | null {
+  const { execSync, existsSync } = opts;
+
+  // Check npm global
+  try {
+    const npmGlobalPrefix = execSync("npm prefix -g 2>/dev/null").trim();
+    const npmGlobalModules = path.join(npmGlobalPrefix, "lib", "node_modules", "clawatch");
+    if (existsSync(npmGlobalModules)) {
+      return { manager: "npm", command: "npm update -g clawatch" };
+    }
+    // Windows-style (no /lib)
+    const npmGlobalModulesAlt = path.join(npmGlobalPrefix, "node_modules", "clawatch");
+    if (existsSync(npmGlobalModulesAlt)) {
+      return { manager: "npm", command: "npm update -g clawatch" };
+    }
+  } catch {
+    /* npm not available */
+  }
+
+  // Check yarn global
+  try {
+    const yarnGlobalDir = execSync("yarn global dir 2>/dev/null").trim();
+    if (yarnGlobalDir && existsSync(path.join(yarnGlobalDir, "node_modules", "clawatch"))) {
+      return { manager: "yarn", command: "yarn global upgrade clawatch" };
+    }
+  } catch {
+    /* yarn not available */
+  }
+
+  // Check pnpm global
+  try {
+    const pnpmGlobalDir = execSync("pnpm root -g 2>/dev/null").trim();
+    if (pnpmGlobalDir && existsSync(path.join(pnpmGlobalDir, "clawatch"))) {
+      return { manager: "pnpm", command: "pnpm update -g clawatch" };
+    }
+  } catch {
+    /* pnpm not available */
+  }
+
+  // Fallback: npm exists → install fresh
+  try {
+    execSync("npm --version 2>/dev/null");
+    return { manager: "npm", command: "npm install -g clawatch@latest" };
+  } catch {
+    /* no npm */
+  }
+
+  return null;
+}
+
+/**
+ * Determine the update action based on current state.
+ */
+export interface UpdateCheckResult {
+  action: "up-to-date" | "update-available" | "check-only" | "no-registry" | "no-version";
+  currentVersion: string;
+  latestVersion?: string;
+  packageManager?: PackageManagerInfo | null;
+}
+
+export function checkForUpdate(opts: {
+  currentVersion: string;
+  latestVersion: string | null;
+  checkOnly: boolean;
+}): UpdateCheckResult {
+  if (!opts.latestVersion) {
+    return {
+      action: "no-version",
+      currentVersion: opts.currentVersion,
+    };
+  }
+
+  const comparison = compareVersions(opts.currentVersion, opts.latestVersion);
+
+  if (comparison === "up-to-date" || comparison === "ahead") {
+    return {
+      action: "up-to-date",
+      currentVersion: opts.currentVersion,
+      latestVersion: opts.latestVersion,
+    };
+  }
+
+  if (opts.checkOnly) {
+    return {
+      action: "check-only",
+      currentVersion: opts.currentVersion,
+      latestVersion: opts.latestVersion,
+    };
+  }
+
+  return {
+    action: "update-available",
+    currentVersion: opts.currentVersion,
+    latestVersion: opts.latestVersion,
+  };
+}