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/src/server.ts

@@ -130,6 +130,13 @@ export interface StartApiOptions {
    * test can prove real timeout behavior deterministically without waiting out the production
    * values. Never set by the executable entry point. */
   readonly nodeServerTimeoutOverride?: Partial<NodeServerTimeouts>;
+  /** Test-only escape hatch: narrows the graceful HTTP drain deadline
+   * (`HTTP_DRAIN_TIMEOUT_MS`) so a forced close can be proven in milliseconds. Never set by the
+   * executable entry point. */
+  readonly drainTimeoutMsOverride?: number;
+  /** Test-only escape hatch: narrows the per-module stop/rollback hook deadline
+   * (`MODULE_STOP_HOOK_TIMEOUT_MS`). Never set by the executable entry point. */
+  readonly moduleHookTimeoutMsOverride?: number;
 }
 
 async function safeCloseDatabase(handle: ApiDatabaseHandle): Promise<void> {
@@ -152,6 +159,94 @@ async function safeStopModuleRuntime(moduleRuntime: StartedModuleRuntime): Promi
   }
 }
 
+/**
+ * The platform's fixed graceful-drain deadline. In-flight HTTP work has this long to finish after
+ * the listener stops accepting new connections; after it, connections are closed so process
+ * shutdown stays bounded. Not configurable in this slice.
+ */
+export const HTTP_DRAIN_TIMEOUT_MS = 30_000;
+
+/**
+ * A shutdown that did not complete cleanly. Carries only fixed booleans and the already-sanitized
+ * module-runtime error — never a request, socket, URL, credential, SQL, or stack detail — so an
+ * operator can see *which* stages failed without any of it becoming a disclosure channel.
+ */
+export class ApiShutdownError extends Error {
+  readonly drainTimedOut: boolean;
+  readonly moduleStopFailed: boolean;
+  readonly moduleStopError: unknown;
+
+  constructor(drainTimedOut: boolean, moduleStopError: unknown) {
+    super("The API did not shut down cleanly.");
+    this.name = "ApiShutdownError";
+    this.drainTimedOut = drainTimedOut;
+    this.moduleStopFailed = moduleStopError !== undefined;
+    this.moduleStopError = moduleStopError;
+    this.stack = `${this.name}: ${this.message}`;
+    Object.freeze(this);
+  }
+}
+
+/**
+ * Stops accepting new connections, then waits up to `timeoutMs` for existing HTTP work to finish.
+ *
+ * At the deadline it closes idle and then still-active connections using Node's own supported
+ * public `Server` APIs (`closeIdleConnections`/`closeAllConnections`, both called only after
+ * `server.close()`), and stops waiting for the close callback. No private socket or server field is
+ * touched.
+ *
+ * Force-closing a connection ends the transport. It does **not** prove that arbitrary in-process
+ * handler JavaScript was canceled — a handler promise may still be running and may still settle.
+ * What is guaranteed is that shutdown no longer waits for it, and that the pool closes afterwards,
+ * so its late database work fails.
+ */
+/** `ServerType` is a union that also covers HTTP/2 servers, which do not expose these two methods.
+ * `serve()` here always creates a plain `http.Server`, which does; narrowing with a real capability
+ * check keeps that honest instead of asserting a cast. */
+interface ConnectionClosingServer {
+  closeAllConnections(): void;
+  closeIdleConnections(): void;
+}
+
+function supportsConnectionClosing(
+  server: ServerType,
+): server is ServerType & ConnectionClosingServer {
+  const candidate = server as Partial<ConnectionClosingServer>;
+  return (
+    typeof candidate.closeIdleConnections === "function" &&
+    typeof candidate.closeAllConnections === "function"
+  );
+}
+
+async function drainHttpServer(
+  server: ServerType,
+  timeoutMs: number,
+): Promise<"drained" | "forced"> {
+  let timer: ReturnType<typeof setTimeout> | undefined;
+  const closed = new Promise<void>((resolve) => {
+    server.close(() => resolve());
+  });
+  try {
+    const outcome = await Promise.race([
+      closed.then(() => "drained" as const),
+      new Promise<"forced">((resolve) => {
+        timer = setTimeout(() => resolve("forced"), timeoutMs);
+      }),
+    ]);
+    if (outcome === "drained") {
+      return "drained";
+    }
+    if (supportsConnectionClosing(server)) {
+      server.closeIdleConnections();
+      server.closeAllConnections();
+    }
+    return "forced";
+  } finally {
+    clearTimeout(timer);
+    // The close callback may still fire later; nothing awaits it, and it carries no rejection.
+  }
+}
+
 /**
  * Binds the Node HTTP server. Two platform-owned transport concerns are applied at this exact
  * boundary, below Hono entirely: `wrapFetchWithClientAddress` resolves and sanitizes the caller's
@@ -292,7 +387,11 @@ export async function startApi(
   // handle to stop here, only the pool this failure leaves open.
   let moduleRuntime: StartedModuleRuntime;
   try {
-    moduleRuntime = await startDiscoveredModuleRuntime(inventory.modules, services);
+    moduleRuntime = await startDiscoveredModuleRuntime(inventory.modules, services, {
+      ...(options.moduleHookTimeoutMsOverride === undefined
+        ? {}
+        : { hookTimeoutMs: options.moduleHookTimeoutMsOverride }),
+    });
   } catch (error) {
     await safeCloseDatabase(databaseHandle);
     throw error;
@@ -345,13 +444,12 @@ export async function startApi(
   // code can run against it afterward. Unlike the startup-cleanup paths above, a module-stop
   // failure here is not swallowed — it is a genuine shutdown result a caller should observe — but
   // database cleanup still always runs first, so a stop failure never leaves the pool open.
+  const drainTimeoutMs = options.drainTimeoutMsOverride ?? HTTP_DRAIN_TIMEOUT_MS;
   let shutdownPromise: Promise<void> | undefined;
   const shutdown = (): Promise<void> => {
     if (!shutdownPromise) {
       shutdownPromise = (async () => {
-        await new Promise<void>((resolve) => {
-          server.close(() => resolve());
-        });
+        const drainOutcome = await drainHttpServer(server, drainTimeoutMs);
         let moduleStopError: unknown;
         try {
           await moduleRuntime.stop();
@@ -359,8 +457,14 @@ export async function startApi(
           moduleStopError = error;
         }
         await safeCloseDatabase(databaseHandle);
-        if (moduleStopError) {
-          throw moduleStopError;
+        // Every stage above ran regardless of what the earlier ones did, so a drain timeout or a
+        // module-stop failure can never leave the pool open. Both failures are reported together,
+        // as fixed metadata: a forced drain is a genuine shutdown failure, not a success.
+        if (drainOutcome === "forced" || moduleStopError) {
+          throw new ApiShutdownError(
+            drainOutcome === "forced",
+            moduleStopError === undefined ? undefined : moduleStopError,
+          );
         }
       })();
     }

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);
+    }
+  });
+});

apps/api/tests/lifecycle.test.ts

@@ -1067,11 +1067,14 @@ describe("Ekklesia API module runtime startup and shutdown", () => {
       issues: [expect.objectContaining({ code: "MODULE_START_FAILED" })],
     });
 
+    // The module whose start hook failed is rolled back first through its own stop hook, then the
+    // module that had already started, in reverse order.
     expect(recorder.events).toEqual([
       "one:register",
       "two:register",
       "one:start",
       "two:start",
+      "two:stop",
       "one:stop",
     ]);
     expect(poolConstructor).toHaveBeenCalledTimes(1);
@@ -1177,8 +1180,14 @@ describe("Ekklesia API module runtime startup and shutdown", () => {
 
     const running = await startApi(validConfig(), { modulesDirectoryOverride: modulesDirectory });
 
+    // Shutdown now aggregates which stages failed; the module-runtime error is carried intact.
     await expect(running.shutdown()).rejects.toMatchObject({
-      issues: [expect.objectContaining({ code: "MODULE_STOP_FAILED", moduleId: "stop-fails" })],
+      drainTimedOut: false,
+      moduleStopError: {
+        issues: [expect.objectContaining({ code: "MODULE_STOP_FAILED", moduleId: "stop-fails" })],
+      },
+      moduleStopFailed: true,
+      name: "ApiShutdownError",
     });
     expect(poolEnd).toHaveBeenCalledTimes(1);
   });

apps/api/tests/module-database.integration.ts

@@ -450,8 +450,15 @@ describe.sequential("live API — module database explicit migration ownership",
       await applyCoreMigrations(database.url);
       resetRecorder();
 
+      // The module whose `start` failed is now rolled back through its own `stop` hook first. That
+      // hook also writes to the table its missing migration would have created, so it fails too —
+      // which is exactly the documented reason a `stop` hook must tolerate partial initialization.
+      // Both outcomes are reported, in order, and neither is swallowed.
       await expect(startMigratedApi(database.url, fixtureModulesDirectory)).rejects.toMatchObject({
-        issues: [expect.objectContaining({ code: "MODULE_START_FAILED", moduleId: "db-facade" })],
+        issues: [
+          expect.objectContaining({ code: "MODULE_START_FAILED", moduleId: "db-facade" }),
+          expect.objectContaining({ code: "MODULE_ROLLBACK_FAILED", moduleId: "db-facade" }),
+        ],
       });
 
       // No schema inference, no automatic table creation as a side effect of the failed attempt.