diff --git a/CHANGELOG.md b/CHANGELOG.md
index f695aa2f8..efef447ec 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -16,6 +16,7 @@
 - Groups: `whatsapp.groups`, `telegram.groups`, and `imessage.groups` now act as allowlists when set. Add `"*"` to keep allow-all behavior.
 
 ### Fixes
+- Skills: harden skill installs with process-group timeouts, clearer timeout messaging, and logged rerun commands when installs fail.
 - Heartbeat: default interval now 30m with a new default prompt + HEARTBEAT.md template.
 - Onboarding: write auth profiles to the multi-agent path (`~/.clawdbot/agents/main/agent/`) so the gateway finds credentials on first startup. Thanks @minghinmatthewlam for PR #327.
 - Docs: add missing `ui:install` setup step in the README. Thanks @hugobarauna for PR #300.
diff --git a/src/agents/skills-install.ts b/src/agents/skills-install.ts
index 0def4ce96..5cfb3df88 100644
--- a/src/agents/skills-install.ts
+++ b/src/agents/skills-install.ts
@@ -27,6 +27,7 @@ export type SkillInstallResult = {
   stdout: string;
   stderr: string;
   code: number | null;
+  command?: string;
 };
 
 function summarizeInstallOutput(text: string): string | undefined {
@@ -55,7 +56,22 @@ function formatInstallFailureMessage(result: {
   code: number | null;
   stdout: string;
   stderr: string;
+  signal?: NodeJS.Signals | null;
+  killed?: boolean;
+  timedOut?: boolean;
+  timeoutMs?: number;
 }): string {
+  const isTimeout =
+    result.timedOut || result.signal === "SIGKILL" || result.killed === true;
+  if (isTimeout) {
+    const seconds =
+      typeof result.timeoutMs === "number"
+        ? Math.max(1, Math.round(result.timeoutMs / 1000))
+        : undefined;
+    return seconds
+      ? `Install timed out after ${seconds}s`
+      : "Install timed out";
+  }
   const code =
     typeof result.code === "number" ? `exit ${result.code}` : "unknown exit";
   const summary =
@@ -127,6 +143,15 @@ function buildInstallCommand(
   }
 }
 
+function formatCommand(argv: string[]): string {
+  return argv
+    .map((arg) => {
+      if (/^[A-Za-z0-9_./:=+-]+$/.test(arg)) return arg;
+      return `'${arg.replace(/'/g, `'\\''`)}'`;
+    })
+    .join(" ");
+}
+
 async function resolveBrewBinDir(
   timeoutMs: number,
 ): Promise<string | undefined> {
@@ -194,6 +219,16 @@ export async function installSkill(
       code: null,
     };
   }
+  if (!command.argv || command.argv.length === 0) {
+    return {
+      ok: false,
+      message: "invalid install command",
+      stdout: "",
+      stderr: "",
+      code: null,
+    };
+  }
+  const commandLine = formatCommand(command.argv);
   if (spec.kind === "brew" && !hasBinary("brew")) {
     return {
       ok: false,
@@ -201,6 +236,7 @@ export async function installSkill(
       stdout: "",
       stderr: "",
       code: null,
+      command: commandLine,
     };
   }
   if (spec.kind === "uv" && !hasBinary("uv")) {
@@ -218,6 +254,7 @@ export async function installSkill(
           stdout: brewResult.stdout.trim(),
           stderr: brewResult.stderr.trim(),
           code: brewResult.code,
+          command: formatCommand(["brew", "install", "uv"]),
         };
       }
     } else {
@@ -227,18 +264,10 @@ export async function installSkill(
         stdout: "",
         stderr: "",
         code: null,
+        command: commandLine,
       };
     }
   }
-  if (!command.argv || command.argv.length === 0) {
-    return {
-      ok: false,
-      message: "invalid install command",
-      stdout: "",
-      stderr: "",
-      code: null,
-    };
-  }
 
   if (spec.kind === "go" && !hasBinary("go")) {
     if (hasBinary("brew")) {
@@ -255,6 +284,7 @@ export async function installSkill(
           stdout: brewResult.stdout.trim(),
           stderr: brewResult.stderr.trim(),
           code: brewResult.code,
+          command: formatCommand(["brew", "install", "go"]),
         };
       }
     } else {
@@ -264,6 +294,7 @@ export async function installSkill(
         stdout: "",
         stderr: "",
         code: null,
+        command: commandLine,
       };
     }
   }
@@ -277,7 +308,14 @@ export async function installSkill(
   const result = await (async () => {
     const argv = command.argv;
     if (!argv || argv.length === 0) {
-      return { code: null, stdout: "", stderr: "invalid install command" };
+      return {
+        code: null,
+        stdout: "",
+        stderr: "invalid install command",
+        signal: null,
+        killed: false,
+        timedOut: false,
+      };
     }
     try {
       return await runCommandWithTimeout(argv, {
@@ -286,16 +324,26 @@ export async function installSkill(
       });
     } catch (err) {
       const stderr = err instanceof Error ? err.message : String(err);
-      return { code: null, stdout: "", stderr };
+      return {
+        code: null,
+        stdout: "",
+        stderr,
+        signal: null,
+        killed: false,
+        timedOut: false,
+      };
     }
   })();
 
-  const success = result.code === 0;
+  const success = result.code === 0 && !result.timedOut;
   return {
     ok: success,
-    message: success ? "Installed" : formatInstallFailureMessage(result),
+    message: success
+      ? "Installed"
+      : formatInstallFailureMessage({ ...result, timeoutMs }),
     stdout: result.stdout.trim(),
     stderr: result.stderr.trim(),
     code: result.code,
+    command: commandLine,
   };
 }
diff --git a/src/commands/onboard-skills.ts b/src/commands/onboard-skills.ts
index 207480379..b121c6b77 100644
--- a/src/commands/onboard-skills.ts
+++ b/src/commands/onboard-skills.ts
@@ -163,6 +163,9 @@ export async function setupSkills(
         spin.stop(
           `Install failed: ${name}${code}${detail ? ` — ${detail}` : ""}`,
         );
+        if (result.command) {
+          runtime.log(`Command: ${result.command}`);
+        }
         if (result.stderr) runtime.log(result.stderr.trim());
         else if (result.stdout) runtime.log(result.stdout.trim());
         runtime.log(
diff --git a/src/process/exec.test.ts b/src/process/exec.test.ts
index 3cb917c3e..0394f4282 100644
--- a/src/process/exec.test.ts
+++ b/src/process/exec.test.ts
@@ -18,5 +18,16 @@ describe("runCommandWithTimeout", () => {
 
     expect(result.code).toBe(0);
     expect(result.stdout).toBe("ok");
+    expect(result.timedOut).toBe(false);
+  });
+
+  it("marks timed out processes", async () => {
+    if (process.platform === "win32") return;
+    const result = await runCommandWithTimeout(
+      [process.execPath, "-e", "setTimeout(() => {}, 1000)"],
+      { timeoutMs: 50 },
+    );
+
+    expect(result.timedOut).toBe(true);
   });
 });
diff --git a/src/process/exec.ts b/src/process/exec.ts
index f0ea1c5a4..ce3530c19 100644
--- a/src/process/exec.ts
+++ b/src/process/exec.ts
@@ -41,6 +41,7 @@ export type SpawnResult = {
   code: number | null;
   signal: NodeJS.Signals | null;
   killed: boolean;
+  timedOut: boolean;
 };
 
 export type CommandOptions = {
@@ -60,18 +61,42 @@ export async function runCommandWithTimeout(
       : optionsOrTimeout;
   const { timeoutMs, cwd, input, env } = options;
 
+  const supportsGroupKill = process.platform !== "win32";
+  const killGraceMs = 5_000;
+
   // Spawn with inherited stdin (TTY) so tools like `pi` stay interactive when needed.
   return await new Promise((resolve, reject) => {
     const child = spawn(argv[0], argv.slice(1), {
       stdio: [input ? "pipe" : "inherit", "pipe", "pipe"],
       cwd,
       env: env ? { ...process.env, ...env } : process.env,
+      detached: supportsGroupKill,
     });
     let stdout = "";
     let stderr = "";
     let settled = false;
+    let timedOut = false;
+    let killTimer: NodeJS.Timeout | undefined;
     const timer = setTimeout(() => {
-      child.kill("SIGKILL");
+      if (settled) return;
+      timedOut = true;
+      const pid = child.pid;
+      if (pid) {
+        try {
+          if (supportsGroupKill) process.kill(-pid, "SIGTERM");
+          else child.kill("SIGTERM");
+        } catch {
+          // ignore
+        }
+        killTimer = setTimeout(() => {
+          try {
+            if (supportsGroupKill) process.kill(-pid, "SIGKILL");
+            else child.kill("SIGKILL");
+          } catch {
+            // ignore
+          }
+        }, killGraceMs);
+      }
     }, timeoutMs);
 
     if (input && child.stdin) {
@@ -89,13 +114,22 @@ export async function runCommandWithTimeout(
       if (settled) return;
       settled = true;
       clearTimeout(timer);
+      if (killTimer) clearTimeout(killTimer);
       reject(err);
     });
     child.on("close", (code, signal) => {
       if (settled) return;
       settled = true;
       clearTimeout(timer);
-      resolve({ stdout, stderr, code, signal, killed: child.killed });
+      if (killTimer) clearTimeout(killTimer);
+      resolve({
+        stdout,
+        stderr,
+        code,
+        signal,
+        killed: child.killed,
+        timedOut,
+      });
     });
   });
 }