diff --git a/src/index.ts b/src/index.ts
index 38c0086..ba0a92a 100644
--- a/src/index.ts
+++ b/src/index.ts
@@ -12,6 +12,7 @@ import type { Config } from "../config.d.ts";
 import { normalizeVerifiedConfig } from "./config.js";
 import { TOOLS } from "./tools/index.js";
 import { RESOURCE_TEMPLATES } from "./mcp/resources.js";
+import { registerServerCleanup } from "./server.js";
 
 import {
   ListResourcesRequestSchema,
@@ -145,6 +146,9 @@ export default function ({ config }: { config: z.infer<typeof configSchema> }) {
   // Create the context, passing server instance and config
   const contextId = randomUUID();
   const context = new Context(server.server, internalConfig, contextId);
+  registerServerCleanup(server.server, () =>
+    context.getSessionManager().closeAllSessions(),
+  );
 
   server.server.registerCapabilities({
     resources: {
diff --git a/src/server.test.ts b/src/server.test.ts
new file mode 100644
index 0000000..a9e8a17
--- /dev/null
+++ b/src/server.test.ts
@@ -0,0 +1,49 @@
+import { describe, expect, it, vi } from "vitest";
+import type { Server } from "@modelcontextprotocol/sdk/server/index.js";
+
+import { registerServerCleanup, ServerList } from "./server.js";
+
+function fakeServer(closeImpl?: () => Promise<void> | void): Server {
+  return {
+    close: vi.fn(closeImpl ?? (async () => undefined)),
+  } as unknown as Server;
+}
+
+describe("ServerList lifecycle cleanup", () => {
+  it("runs registered session cleanup before closing a server", async () => {
+    const cleanup = vi.fn(async () => undefined);
+    const server = fakeServer();
+    registerServerCleanup(server, cleanup);
+
+    const serverList = new ServerList(async () => server);
+    const created = await serverList.create();
+
+    await serverList.close(created);
+
+    expect(cleanup).toHaveBeenCalledOnce();
+    expect(server.close).toHaveBeenCalledOnce();
+    expect(cleanup.mock.invocationCallOrder[0]).toBeLessThan(
+      vi.mocked(server.close).mock.invocationCallOrder[0],
+    );
+  });
+
+  it("keeps closeAll idempotent when a transport close re-enters ServerList.close", async () => {
+    let created!: Server;
+    const serverList = new ServerList(async () => {
+      created = fakeServer(async () => {
+        await serverList.close(created);
+      });
+      return created;
+    });
+    const cleanup = vi.fn(async () => undefined);
+
+    const server = await serverList.create();
+    registerServerCleanup(server, cleanup);
+
+    await serverList.closeAll();
+    await serverList.closeAll();
+
+    expect(cleanup).toHaveBeenCalledOnce();
+    expect(server.close).toHaveBeenCalledOnce();
+  });
+});
diff --git a/src/server.ts b/src/server.ts
index 1c5b833..7f0313f 100644
--- a/src/server.ts
+++ b/src/server.ts
@@ -1,7 +1,19 @@
 import { Server } from "@modelcontextprotocol/sdk/server/index.js";
 
+type ServerCleanup = () => Promise<void> | void;
+
+const serverCleanups = new WeakMap<Server, ServerCleanup>();
+
+export function registerServerCleanup(
+  server: Server,
+  cleanup: ServerCleanup,
+) {
+  serverCleanups.set(server, cleanup);
+}
+
 export class ServerList {
   private _servers: Server[] = [];
+  private _closing = new WeakSet<Server>();
   private _serverFactory: () => Promise<Server>;
 
   constructor(serverFactory: () => Promise<Server>) {
@@ -15,12 +27,26 @@ export class ServerList {
   }
 
   async close(server: Server) {
-    await server.close();
+    if (this._closing.has(server)) return;
+
     const index = this._servers.indexOf(server);
-    if (index !== -1) this._servers.splice(index, 1);
+    if (index === -1) return;
+
+    this._closing.add(server);
+    this._servers.splice(index, 1);
+
+    try {
+      await serverCleanups.get(server)?.();
+    } finally {
+      try {
+        await server.close();
+      } finally {
+        this._closing.delete(server);
+      }
+    }
   }
 
   async closeAll() {
-    await Promise.all(this._servers.map((server) => server.close()));
+    await Promise.all([...this._servers].map((server) => this.close(server)));
   }
 }
diff --git a/src/transport.ts b/src/transport.ts
index 4885bf9..b6adfb1 100644
--- a/src/transport.ts
+++ b/src/transport.ts
@@ -53,10 +53,13 @@ async function handleStreamable(
       sessionIdGenerator: () => sessionId,
     });
     sessions.set(sessionId, transport);
+    const server = await serverList.create();
     transport.onclose = () => {
       if (transport.sessionId) sessions.delete(transport.sessionId);
+      void serverList.close(server).catch((error: unknown) => {
+        console.error("Error closing HTTP MCP session:", error);
+      });
     };
-    const server = await serverList.create();
     await server.connect(transport);
     return await transport.handleRequest(req, res);
   }