diff --git a/changelog.d/fixes/0000-skills-timeout-status.md b/changelog.d/fixes/0000-skills-timeout-status.md
new file mode 100644
index 0000000000..ad33867634
--- /dev/null
+++ b/changelog.d/fixes/0000-skills-timeout-status.md
@@ -0,0 +1 @@
+- **fix(skills):** a skill that outlives the executor timeout is now recorded as `timeout` instead of `error`, so execution history and analytics can tell timeouts from handler failures. The race timer is also cleared once the handler settles; it used to stay pending for the full timeout (30 s by default) after every execution.
diff --git a/src/lib/skills/executor.ts b/src/lib/skills/executor.ts
index 06cc96a646..e39bdfb93b 100644
--- a/src/lib/skills/executor.ts
+++ b/src/lib/skills/executor.ts
@@ -13,6 +13,13 @@ import { logger } from "../../../open-sse/utils/logger.ts";
 
 const log = logger("SKILLS_EXECUTOR");
 
+class SkillTimeoutError extends Error {
+  constructor() {
+    super("Skill execution timed out");
+    this.name = "SkillTimeoutError";
+  }
+}
+
 function toSafeSkillErrorMessage(value: unknown): string {
   try {
     const raw = value instanceof Error ? value.message : value;
@@ -286,12 +293,15 @@ class SkillExecutor {
   }
 
   private async executeWithTimeout<T>(promise: Promise<T>): Promise<T> {
-    return Promise.race([
-      promise,
-      new Promise<T>((_, reject) =>
-        setTimeout(() => reject(new Error("Skill execution timed out")), this.timeout)
-      ),
-    ]);
+    let timer: ReturnType<typeof setTimeout> | undefined;
+    const timeout = new Promise<never>((_, reject) => {
+      timer = setTimeout(() => reject(new SkillTimeoutError()), this.timeout);
+    });
+    try {
+      return await Promise.race([promise, timeout]);
+    } finally {
+      clearTimeout(timer);
+    }
   }
 
   /**
@@ -343,7 +353,7 @@ class SkillExecutor {
       }
     } catch (err) {
       errorMessage = toSafeSkillErrorMessage(err);
-      status = SkillStatus.ERROR;
+      status = err instanceof SkillTimeoutError ? SkillStatus.TIMEOUT : SkillStatus.ERROR;
     }
 
     return { output, errorMessage, status };
diff --git a/tests/unit/characterization-skills.test.ts b/tests/unit/characterization-skills.test.ts
index 93a22fc7b5..4d5c881447 100644
--- a/tests/unit/characterization-skills.test.ts
+++ b/tests/unit/characterization-skills.test.ts
@@ -31,8 +31,7 @@ function uniqueName(prefix: string) {
   return `${prefix}-${randomUUID().slice(0, 8)}`;
 }
 
-// Short executor timeout so the timeout case runs fast. NOTE: executeWithTimeout never
-// clears its timer, so every execution leaves a pending timer of this length behind.
+// Short executor timeout so the timeout case runs fast.
 skillExecutor.setTimeout(200);
 
 skillExecutor.registerHandler("char-echo", async (input) => ({ echoed: String(input.text) }));
@@ -323,7 +322,7 @@ test("execute: a failure-shaped output and a throwing handler both resolve with
   assert.equal(hardRun.output, null);
 });
 
-test("characterization: a timed-out skill is currently recorded as status error, never timeout", async () => {
+test("a timed-out skill is recorded as status timeout", async () => {
   const name = uniqueName("char-slow");
   await skillRegistry.register({
     name,
@@ -332,9 +331,8 @@ test("characterization: a timed-out skill is currently recorded as status error,
     apiKeyId: "char-slow",
   });
   const run = await skillExecutor.execute(name, {}, { apiKeyId: "char-slow" });
-  // SkillStatus.TIMEOUT exists and the DB CHECK allows 'timeout', but the executor maps a
-  // timeout to ERROR with this message.
-  assert.equal(run.status, SkillStatus.ERROR);
+  // A timeout is recorded as SkillStatus.TIMEOUT (#16187), not as a generic handler error.
+  assert.equal(run.status, SkillStatus.TIMEOUT);
   assert.equal(run.errorMessage, "Skill execution timed out");
 });
 
diff --git a/tests/unit/skills-executor-timeout.test.ts b/tests/unit/skills-executor-timeout.test.ts
new file mode 100644
index 0000000000..247fce608b
--- /dev/null
+++ b/tests/unit/skills-executor-timeout.test.ts
@@ -0,0 +1,57 @@
+import test from "node:test";
+import assert from "node:assert/strict";
+import { randomUUID } from "node:crypto";
+import "../_setup/isolateDataDir.ts";
+
+process.env.DISABLE_SQLITE_AUTO_BACKUP ||= "true";
+
+const core = await import("../../src/lib/db/core.ts");
+const { skillRegistry } = await import("../../src/lib/skills/registry.ts");
+const { skillExecutor } = await import("../../src/lib/skills/executor.ts");
+const { SkillStatus } = await import("../../src/lib/skills/types.ts");
+
+const SCHEMA = { input: {}, output: {} };
+const API_KEY_ID = "executor-timeout";
+
+skillExecutor.registerHandler("timeout-fast", async () => ({ ok: true }));
+skillExecutor.registerHandler("timeout-slow", () => new Promise(() => {}));
+
+test.after(() => {
+  core.resetDbInstance();
+});
+
+function pendingTimers(): number {
+  return process.getActiveResourcesInfo().filter((name) => name === "Timeout").length;
+}
+
+async function registerSkill(handler: string) {
+  const name = `${handler}-${randomUUID().slice(0, 8)}`;
+  await skillRegistry.register({ name, schema: SCHEMA, handler, apiKeyId: API_KEY_ID });
+  return name;
+}
+
+test("a skill that outlives the executor timeout is recorded as timeout and persisted that way", async () => {
+  skillExecutor.setTimeout(100);
+  const name = await registerSkill("timeout-slow");
+  const run = await skillExecutor.execute(name, {}, { apiKeyId: API_KEY_ID });
+  assert.equal(run.status, SkillStatus.TIMEOUT);
+  assert.equal(run.errorMessage, "Skill execution timed out");
+
+  const row = core
+    .getDbInstance()
+    .prepare("SELECT status FROM skill_executions WHERE id = ?")
+    .get(run.id) as { status: string };
+  assert.equal(row.status, "timeout");
+});
+
+test("a handler that settles in time leaves no pending timeout timer behind", async () => {
+  skillExecutor.setTimeout(30_000);
+  const name = await registerSkill("timeout-fast");
+  const before = pendingTimers();
+  const run = await skillExecutor.execute(name, {}, { apiKeyId: API_KEY_ID });
+  assert.equal(run.status, SkillStatus.SUCCESS);
+  assert.ok(
+    pendingTimers() <= before,
+    "the 30s race timer must be cleared once the handler settles"
+  );
+});
diff --git a/tests/unit/skills-executor.test.ts b/tests/unit/skills-executor.test.ts
index 7a95793745..28cb87f111 100644
--- a/tests/unit/skills-executor.test.ts
+++ b/tests/unit/skills-executor.test.ts
@@ -242,7 +242,7 @@ test("skillExecutor records disabled skills and missing skills as direct failure
   assert.equal(skillExecutor.listExecutions("key-a").length, 0);
 });
 
-test("skillExecutor turns handler errors and timeouts into error executions", async () => {
+test("skillExecutor records handler errors as error and timeouts as timeout", async () => {
   await registerEchoSkill();
 
   skillExecutor.registerHandler("echo-handler", async () => {
@@ -289,7 +289,7 @@ test("skillExecutor turns handler errors and timeouts into error executions", as
   );
 
   assert.equal(skillExecutor["maxRetries"], 7);
-  assert.equal(timedOut.status, "error");
+  assert.equal(timedOut.status, "timeout");
   assert.equal(timedOut.output, null);
   assert.match(timedOut.errorMessage, /timed out/i);
 });