diff --git a/bin/openpi.js b/bin/openpi.js
index 62d9d72a..5c5eeaf8 100755
--- a/bin/openpi.js
+++ b/bin/openpi.js
@@ -95,6 +95,20 @@ try {
       : {}),
   });
   await host.start();
+  const onStopSignal = () => {
+    void stop().then(
+      () => process.exit(0),
+      (error) => {
+        console.error(
+          `Failed to stop OpenPI Web Workbench: ${error instanceof Error ? error.message : String(error)}`,
+        );
+        process.exit(1);
+      },
+    );
+  };
+  for (const signal of ["SIGINT", "SIGTERM"]) {
+    process.once(signal, onStopSignal);
+  }
   traceWeb("web_started", {
     ...(runtime.workspaceSelected === true ? { cwd: runtime.cwd } : {}),
     origin: host.origin,
@@ -112,20 +126,6 @@ try {
     console.log(`OpenPI Web Workbench is running at ${host.origin}`);
     if (!opened) console.log(`Open this URL in a browser: ${host.url}`);
   }
-
-  for (const signal of ["SIGINT", "SIGTERM"]) {
-    process.once(signal, () => {
-      void stop().then(
-        () => process.exit(0),
-        (error) => {
-          console.error(
-            `Failed to stop OpenPI Web Workbench: ${error instanceof Error ? error.message : String(error)}`,
-          );
-          process.exit(1);
-        },
-      );
-    });
-  }
 } catch (error) {
   let cleanupError;
   try {
diff --git a/tests/web/cli.test.ts b/tests/web/cli.test.ts
index 845067e3..5e0dae65 100644
--- a/tests/web/cli.test.ts
+++ b/tests/web/cli.test.ts
@@ -1,6 +1,7 @@
 import assert from "node:assert/strict";
 import { execFile, spawn } from "node:child_process";
 import { once } from "node:events";
+import { watch } from "node:fs";
 import {
   cp,
   mkdir,
@@ -10,12 +11,76 @@ import {
   stat,
   writeFile,
 } from "node:fs/promises";
-import { join } from "node:path";
+import { dirname, join } from "node:path";
 import { fileURLToPath } from "node:url";
 import { promisify } from "node:util";
 import test from "node:test";
 
 const execFileAsync = promisify(execFile);
+
+async function inspectPath(path: string) {
+  try {
+    return { exists: true, content: await readFile(path, "utf8") };
+  } catch (error) {
+    return {
+      exists: false,
+      error:
+        error instanceof Error && "code" in error
+          ? String(error.code)
+          : String(error),
+    };
+  }
+}
+
+// Same-dir write-then-rename makes the final name appear only after
+// contents are complete. Directory watch can fire first for the staging
+// name and miss the rename; also wake from the writer's stderr.
+function waitForPublishedMarker(
+  path: string,
+  expected: string,
+  timeoutMs: number,
+  diagnostics: () => string,
+  wake?: NodeJS.ReadableStream,
+) {
+  return new Promise<void>((resolve, reject) => {
+    let settled = false;
+    const finish = (error?: Error) => {
+      if (settled) return;
+      settled = true;
+      clearTimeout(timer);
+      watcher.close();
+      wake?.off("data", tryRead);
+      if (error) reject(error);
+      else resolve();
+    };
+    const tryRead = () => {
+      void readFile(path, "utf8").then(
+        (content) => {
+          if (content === expected) finish();
+        },
+        () => {},
+      );
+    };
+    const timer = setTimeout(() => {
+      void Promise.all([inspectPath(path), inspectPath(`${path}.tmp`)]).then(
+        ([marker, staging]) => {
+          finish(
+            new Error(
+              `timed out waiting for ${path} contents; marker=${JSON.stringify(marker)} staging=${JSON.stringify(staging)}; ${diagnostics()}`,
+            ),
+          );
+        },
+      );
+    }, timeoutMs);
+    const watcher = watch(dirname(path), tryRead);
+    watcher.on("error", (error) => {
+      finish(new Error(`watch error for ${path}: ${error}; ${diagnostics()}`));
+    });
+    wake?.on("data", tryRead);
+    tryRead();
+  });
+}
+
 const entrypoint = new URL("../../bin/openpi.js", import.meta.url);
 const entrypointPath = fileURLToPath(entrypoint);
 const staticAssetsPath = fileURLToPath(
@@ -36,6 +101,21 @@ test("openpi is an executable standalone Web entrypoint", async () => {
   assert.match(stdout, /never enter an interactive terminal Pi session/u);
 });
 
+test("CLI registers stop signals before printing readiness", async () => {
+  const source = await readFile(entrypointPath, "utf8");
+  const handlers = source.indexOf("process.once(signal, onStopSignal)");
+  const workspaceReady = source.indexOf(
+    "OpenPI Web Workbench is running at ${host.origin}",
+  );
+  const unboundReady = source.indexOf("formatWebReadyScreen(");
+  assert.notEqual(handlers, -1);
+  assert.notEqual(workspaceReady, -1);
+  assert.notEqual(unboundReady, -1);
+  assert.ok(handlers < workspaceReady);
+  assert.ok(handlers < unboundReady);
+  assert.equal(source.includes("process.on(signal, onStopSignal)"), false);
+});
+
 test("installed CLI loads TypeScript Web modules through its package loader", async () => {
   const temporaryRoot = await mkdtemp(join(process.cwd(), ".openpi-cli-test-"));
   const packageRoot = join(temporaryRoot, "node_modules", "@tt-a1i", "openpi");
@@ -195,34 +275,44 @@ export class PiWebRuntime {
       child.stderr.setEncoding("utf8");
       let signalOutput = "";
       let signalError = "";
-      child.stdout.on("data", (chunk) => {
-        signalOutput += chunk;
-      });
+      const closed = once(child, "close") as Promise<
+        [number | null, NodeJS.Signals | null]
+      >;
       child.stderr.on("data", (chunk) => {
         signalError += chunk;
       });
-      await new Promise<void>((resolve, reject) => {
+      const started = new Promise<void>((resolve, reject) => {
         const timeout = setTimeout(
           () => reject(new Error("installed CLI did not start")),
           5_000,
         );
-        const waitForReady = () => {
+        let sentStop = false;
+        const onStdout = (chunk: string) => {
+          signalOutput += chunk;
           if (
-            signalOutput.includes(
+            sentStop ||
+            !signalOutput.includes(
               "OpenPI Web Workbench is running at http://127.0.0.1:12345",
             )
           ) {
-            clearTimeout(timeout);
-            resolve();
             return;
           }
-          setTimeout(waitForReady, 10);
+          sentStop = true;
+          child.stdout.off("data", onStdout);
+          clearTimeout(timeout);
+          child.kill("SIGTERM");
+          resolve();
         };
-        waitForReady();
+        child.stdout.on("data", onStdout);
       });
-      child.kill("SIGTERM");
-      const [exitCode] = (await once(child, "close")) as [number | null];
-      assert.equal(exitCode, 1);
+      await started;
+      const [exitCode, signal] = await closed;
+      assert.equal(
+        exitCode,
+        1,
+        `expected process.exit(1) after stop failure, got code=${String(exitCode)} signal=${String(signal)} stderr=${signalError}`,
+      );
+      assert.equal(signal, null);
       assert.match(
         signalError,
         /Failed to stop OpenPI Web Workbench: stop failed/u,
@@ -232,3 +322,167 @@ export class PiWebRuntime {
     await rm(temporaryRoot, { recursive: true, force: true });
   }
 });
+
+test("a second SIGTERM uses default termination while stop is in flight", async () => {
+  if (process.platform === "win32") return;
+  const temporaryRoot = await mkdtemp(join(process.cwd(), ".openpi-cli-test-"));
+  const packageRoot = join(temporaryRoot, "node_modules", "@tt-a1i", "openpi");
+  const stopMarker = join(temporaryRoot, "stop-entered");
+  let child: ReturnType<typeof spawn> | undefined;
+  let output = "";
+  let errorOutput = "";
+  try {
+    await mkdir(join(packageRoot, "bin"), { recursive: true });
+    await mkdir(join(packageRoot, "web", "host"), { recursive: true });
+    await mkdir(join(packageRoot, "web", "runtime"), { recursive: true });
+    await cp(entrypointPath, join(packageRoot, "bin", "openpi.js"));
+    await writeFile(
+      join(packageRoot, "package.json"),
+      JSON.stringify({ type: "module" }),
+    );
+    await writeFile(
+      join(packageRoot, "web", "host", "browser-launcher.ts"),
+      "export async function openBrowser(): Promise<boolean> { return false; }\n",
+    );
+    await writeFile(
+      join(packageRoot, "web", "host", "terminal-status.ts"),
+      "export function formatWebReadyScreen(options: { origin: string; url: string }): string { return `ready ${options.origin} ${options.url}`; }\n",
+    );
+    await writeFile(
+      join(packageRoot, "web", "host", "web-host.ts"),
+      `import { rename, writeFile } from "node:fs/promises";
+
+export class WebHost {
+  origin = "http://127.0.0.1:12348";
+  url = "http://127.0.0.1:12348/";
+  hang: ReturnType<typeof setInterval> | undefined;
+  async start(): Promise<void> {
+    this.hang = setInterval(() => undefined, 60_000);
+  }
+  async stop(): Promise<void> {
+    const marker = process.env.OPENPI_CLI_STOP_ENTERED_MARKER;
+    if (marker) {
+      const staging = \`\${marker}.tmp\`;
+      await writeFile(staging, "entered");
+      await rename(staging, marker);
+      process.stderr.write("stop-entered\\n");
+    }
+    this.hang ??= setInterval(() => undefined, 60_000);
+    await new Promise(() => {});
+  }
+}\n`,
+    );
+    await writeFile(
+      join(packageRoot, "web", "trace.ts"),
+      "export function traceWeb(): void {}\n",
+    );
+    await writeFile(
+      join(packageRoot, "web", "runtime", "pi-runtime.ts"),
+      `export class PiWebRuntime {
+  static async create(cwd: string): Promise<{ cwd: string; dispose(): Promise<void> }> {
+    return { cwd, async dispose(): Promise<void> {} };
+  }
+}\n`,
+    );
+
+    child = spawn(
+      process.execPath,
+      [
+        join(packageRoot, "bin", "openpi.js"),
+        "web",
+        temporaryRoot,
+        "--no-open",
+      ],
+      {
+        env: {
+          ...process.env,
+          OPENPI_CLI_STOP_ENTERED_MARKER: stopMarker,
+        },
+        stdio: ["ignore", "pipe", "pipe"],
+      },
+    );
+    const stdout = child.stdout;
+    const stderr = child.stderr;
+    assert.ok(stdout);
+    assert.ok(stderr);
+    stdout.setEncoding("utf8");
+    stderr.setEncoding("utf8");
+    stdout.on("data", (chunk) => {
+      output += chunk;
+    });
+    stderr.on("data", (chunk) => {
+      errorOutput += chunk;
+    });
+    let firstKill: boolean | undefined;
+    const diagnostics = () =>
+      `firstKill=${String(firstKill)} code=${String(child?.exitCode)} signal=${String(child?.signalCode)} stdout=${output} stderr=${errorOutput}`;
+    const closed = once(child, "close") as Promise<
+      [number | null, NodeJS.Signals | null]
+    >;
+    await new Promise<void>((resolve, reject) => {
+      const timeout = setTimeout(() => {
+        reject(new Error(`installed CLI did not start; ${diagnostics()}`));
+      }, 5_000);
+      let sentFirst = false;
+      const onStdout = () => {
+        if (
+          sentFirst ||
+          !output.includes(
+            "OpenPI Web Workbench is running at http://127.0.0.1:12348",
+          )
+        ) {
+          return;
+        }
+        sentFirst = true;
+        stdout.off("data", onStdout);
+        clearTimeout(timeout);
+        firstKill = child?.kill("SIGTERM");
+        resolve();
+      };
+      stdout.on("data", onStdout);
+    });
+    assert.equal(
+      firstKill,
+      true,
+      `first SIGTERM not delivered; ${diagnostics()}`,
+    );
+    await waitForPublishedMarker(
+      stopMarker,
+      "entered",
+      5_000,
+      diagnostics,
+      stderr,
+    );
+    assert.equal(await readFile(stopMarker, "utf8"), "entered");
+    child.kill("SIGTERM");
+    const [exitCode, signal] = await Promise.race([
+      closed,
+      new Promise<[number | null, NodeJS.Signals | null]>((_, reject) => {
+        setTimeout(() => {
+          reject(
+            new Error(
+              `child did not exit after second SIGTERM; ${diagnostics()}`,
+            ),
+          );
+        }, 5_000);
+      }),
+    ]);
+    assert.equal(
+      exitCode,
+      null,
+      `expected default SIGTERM, got code=${String(exitCode)} signal=${String(signal)} stdout=${output} stderr=${errorOutput}`,
+    );
+    assert.equal(signal, "SIGTERM");
+  } finally {
+    if (child && child.exitCode === null && child.signalCode === null) {
+      child.kill("SIGKILL");
+      await Promise.race([
+        once(child, "close"),
+        new Promise((resolve) => {
+          setTimeout(resolve, 1_000);
+        }),
+      ]);
+    }
+    await rm(temporaryRoot, { recursive: true, force: true });
+  }
+});