fix: bound module lifecycle shutdown

Nothing bounded shutdown, and a module that failed to start was never cleaned up.

`startModules` appended to its rollback set only after `start()` resolved, so a
hook that acquired a connection, registered a listener, or recorded partial
initialization and then threw had its own `stop()` skipped, while every
previously completed module was rolled back correctly. A module now joins the
rollback set the moment its start hook is invoked: its own stop hook runs first,
then earlier modules in reverse order. The original start issue stays first in
the reported issues, and a failure stopping the failing module is appended
without preventing the rest of the rollback. The consequence for module authors
is explicit and documented — `stop()` may run after a partially completed
`start()` and must be safe and idempotent about resources it may or may not
hold.

Neither stage of shutdown had a deadline. `shutdown()` awaited `server.close()`
with no bound, so one open connection could hold it forever, and each stop or
rollback hook was awaited without a bound, so a hook that never settled kept the
pool open indefinitely. Both now have fixed, non-configurable defaults: 10
seconds per module hook and 30 seconds for the graceful HTTP drain. A hook that
reaches its deadline records MODULE_STOP_TIMEOUT or MODULE_ROLLBACK_TIMEOUT and
the sequence continues with the next module, so the whole stop sequence is
finite in the started module count rather than one global ten-second bound.
Timers that lose the race are cleared, the losing promise gets a permanent
rejection handler so a late throw cannot become an unhandled rejection, and a
timed-out hook is never awaited again.

At the drain deadline the platform closes idle and then active connections
through Node's own public closeIdleConnections/closeAllConnections, after
server.close(), touching no private field, and stops waiting for the close
callback. It then runs the bounded module stop sequence and closes the pool, so
a drain timeout or a stop failure never skips later cleanup. Both are reported
together as an ApiShutdownError carrying only fixed booleans and the already
sanitized module error; a forced drain is a shutdown failure, not a success.

Stated honestly rather than overstated: a deadline bounds how long the platform
waits, not how long module code runs. An in-process promise cannot be canceled,
and closing a socket does not prove a handler promise ended. What is guaranteed
is that shutdown stops waiting and the pool closes afterwards, so late database
work fails.

Co-Authored-By: Claude Opus 5 <[email protected]>

apps/api/tests/api-http.integration.ts

@@ -336,6 +336,8 @@ function apiOrigin(running: RunningApi): string {
 
 interface StartConfiguredApiOptions {
   readonly clientAddress?: ClientAddressConfigInput;
+  /** Test-only narrowing of the platform's 30-second graceful HTTP drain deadline. */
+  readonly drainTimeoutMsOverride?: number;
   readonly modulesDirectoryOverride?: string;
   readonly nodeServerTimeoutOverride?: Partial<NodeServerTimeouts>;
   /** Defaults to `true`: almost every existing scenario in this suite signs accounts up over HTTP
@@ -391,6 +393,9 @@ async function startConfiguredApi(
     ...(options.nodeServerTimeoutOverride === undefined
       ? {}
       : { nodeServerTimeoutOverride: options.nodeServerTimeoutOverride }),
+    ...(options.drainTimeoutMsOverride === undefined
+      ? {}
+      : { drainTimeoutMsOverride: options.drainTimeoutMsOverride }),
   });
 }
 
@@ -2725,3 +2730,114 @@ describe.sequential("live API — Node header/request timeouts and client errors
     expect(logs.join("\n")).not.toContain("zzz");
   });
 });
+
+/**
+ * Pass 4: shutdown is finite even when HTTP work does not settle.
+ *
+ * These drive a real bound listener and a real socket rather than a mock, because the behavior
+ * under test is what Node's own `server.close()` does and does not do. Every socket, server, and
+ * disposable database is closed in `finally`, and each scenario carries its own outer deadline so
+ * a regression fails rather than hangs.
+ */
+describe.sequential("live API — bounded HTTP drain and shutdown", () => {
+  async function withDeadline<T>(operation: Promise<T>, timeoutMs: number): Promise<T> {
+    let timer: ReturnType<typeof setTimeout> | undefined;
+    try {
+      return await Promise.race([
+        operation,
+        new Promise<never>((_resolve, reject) => {
+          timer = setTimeout(
+            () => reject(harnessError("shutdown did not settle in time")),
+            timeoutMs,
+          );
+        }),
+      ]);
+    } finally {
+      clearTimeout(timer);
+    }
+  }
+
+  it("serves a real request and then drains cleanly, well inside the deadline", async () => {
+    const database = await createDisposableDatabase("drain_ok");
+    await applyCoreMigrations(database.url);
+    const running = await startConfiguredApi(database.url, { drainTimeoutMsOverride: 5_000 });
+    try {
+      const origin = apiOrigin(running);
+      const response = await fetch(`${origin}/api/v1/principal`);
+      expect(response.status).toBe(200);
+      expect(await response.json()).toEqual({ kind: "anonymous" });
+
+      // Nothing is stalled, so the graceful path completes and shutdown reports success — the
+      // drain deadline is never reached and no connection is force-closed.
+      await expect(withDeadline(running.shutdown(), 20_000)).resolves.toBeUndefined();
+
+      // The listener really is closed afterwards.
+      await expect(fetch(`${origin}/api/v1/principal`)).rejects.toBeTruthy();
+    } finally {
+      await running.shutdown().catch(() => undefined);
+      await dropDatabase(database.name);
+    }
+  });
+
+  it("force-closes a stalled connection at the drain deadline and still reaches pool closure", async () => {
+    const database = await createDisposableDatabase("drain_forced");
+    await applyCoreMigrations(database.url);
+    // A short, test-only drain deadline; production keeps HTTP_DRAIN_TIMEOUT_MS unchanged.
+    const running = await startConfiguredApi(database.url, { drainTimeoutMsOverride: 250 });
+    const address = running.server.address();
+    if (!address || typeof address !== "object") {
+      throw harnessError("The API integration server has no bound address.");
+    }
+    const socket = net.connect({ host: "127.0.0.1", port: address.port });
+    try {
+      // A real, deliberately incomplete request: headers are never finished, so Node keeps the
+      // connection open and `server.close()` alone would wait indefinitely.
+      await new Promise<void>((resolve, reject) => {
+        socket.once("error", reject);
+        socket.on("data", () => undefined);
+        socket.write("GET /api/v1/principal HTTP/1.1\r\nHost: 127.0.0.1\r\n", () => resolve());
+      });
+
+      const closed = new Promise<void>((resolve) => {
+        socket.once("close", () => resolve());
+      });
+
+      let captured: unknown;
+      try {
+        await withDeadline(running.shutdown(), 20_000);
+      } catch (error) {
+        captured = error;
+      }
+
+      // A forced drain is a genuine shutdown failure, never reported as success.
+      expect(captured).toMatchObject({ drainTimedOut: true, name: "ApiShutdownError" });
+      // ...and it still carries nothing about the request, socket, or database.
+      const publicText = `${String(captured)}\n${(captured as Error).stack ?? ""}`;
+      expect(publicText).not.toContain("127.0.0.1");
+      expect(publicText).not.toContain(database.name);
+      // The connection was actually closed by the platform, not left dangling.
+      await withDeadline(closed, 10_000);
+    } finally {
+      socket.destroy();
+      await running.shutdown().catch(() => undefined);
+      await dropDatabase(database.name);
+    }
+  });
+
+  it("shares one memoized shutdown across concurrent callers", async () => {
+    const database = await createDisposableDatabase("drain_once");
+    await applyCoreMigrations(database.url);
+    const running = await startConfiguredApi(database.url, { drainTimeoutMsOverride: 5_000 });
+    try {
+      const [first, second, third] = await withDeadline(
+        Promise.all([running.shutdown(), running.shutdown(), running.shutdown()]),
+        20_000,
+      );
+      expect([first, second, third]).toEqual([undefined, undefined, undefined]);
+      // A later caller observes the same completed result rather than restarting cleanup.
+      await expect(running.shutdown()).resolves.toBeUndefined();
+    } finally {
+      await dropDatabase(database.name);
+    }
+  });
+});