diff --git a/src/js/node/net.ts b/src/js/node/net.ts
index 904facfe16b6..b0a0d7f36b22 100644
--- a/src/js/node/net.ts
+++ b/src/js/node/net.ts
@@ -4084,26 +4084,6 @@ Server.prototype[kRealListen] = function (
       data: this,
       pauseOnConnect: this.pauseOnConnect,
     });
-    // Mirror libuv uv_pipe_chmod: readableAll/writableAll relax the unix socket
-    // file's group/other permission bits. Skipped on Windows and abstract
-    // sockets (no filesystem entry). uSockets binds synchronously, so the file
-    // exists by the time Bun.listen returns.
-    // https://github.com/nodejs/node/blob/614050b657e9757c1097aa85f92f2cb51149dc0d/lib/net.js#L1899
-    if ((readableAll || writableAll) && process.platform !== "win32" && path.charCodeAt(0) !== 0) {
-      let desired = 0;
-      if (readableAll) desired |= 0o44; // S_IRGRP | S_IROTH
-      if (writableAll) desired |= 0o22; // S_IWGRP | S_IWOTH
-      try {
-        const fs = require("node:fs");
-        const cur = fs.statSync(path).mode;
-        if ((cur & desired) !== desired) fs.chmodSync(path, cur | desired);
-      } catch (e) {
-        // _handle is a Bun.listen SocketListener: it exposes stop(), not close().
-        this._handle?.stop?.(true);
-        this._handle = null;
-        throw e;
-      }
-    }
   } else if (fd != null) {
     this._handle = Bun.listen({
       fd,
@@ -4117,6 +4097,9 @@ Server.prototype[kRealListen] = function (
       data: this,
       pauseOnConnect: this.pauseOnConnect,
     });
+    // The native listener owns the fd now, so the cluster handle must not close it.
+    const clusterHandle = this[kClusterHandle];
+    if (clusterHandle != null && clusterHandle.sharedFd === fd) clusterHandle.adopted = true;
   } else {
     this._handle = Bun.listen({
       port,
@@ -4132,21 +4115,38 @@ Server.prototype[kRealListen] = function (
     });
   }
 
-  this._handle[owner_symbol] = this;
-  this._handle.onconnection = onconnection;
+  try {
+    // uv_pipe_chmod: https://github.com/nodejs/node/blob/614050b657e9757c1097aa85f92f2cb51149dc0d/lib/net.js#L1899
+    if (path && (readableAll || writableAll) && process.platform !== "win32" && path.charCodeAt(0) !== 0) {
+      let desired = 0;
+      if (readableAll) desired |= 0o44; // S_IRGRP | S_IROTH
+      if (writableAll) desired |= 0o22; // S_IWGRP | S_IWOTH
+      const fs = require("node:fs");
+      const cur = fs.statSync(path).mode;
+      if ((cur & desired) !== desired) fs.chmodSync(path, cur | desired);
+    }
 
-  const addr = this.address();
-  if (addr && typeof addr === "object") {
-    const familyLast = String(addr.family).slice(-1);
-    this._connectionKey = `${familyLast}:${addr.address}:${port}`;
-  }
+    this._handle[owner_symbol] = this;
+    this._handle.onconnection = onconnection;
 
-  if (contexts) {
-    for (const [name, context] of contexts) {
-      // tls.ts stores the InternalSecureContext wrapper; the native side wants
-      // the native SSL_CTX wrapper at `.context`.
-      addServerName(this._handle, name, context.context ?? context);
+    const addr = this.address();
+    if (addr && typeof addr === "object") {
+      const familyLast = String(addr.family).slice(-1);
+      this._connectionKey = `${familyLast}:${addr.address}:${port}`;
     }
+
+    if (contexts) {
+      for (const [name, context] of contexts) {
+        // tls.ts stores the InternalSecureContext wrapper; the native side wants
+        // the native SSL_CTX wrapper at `.context`.
+        addServerName(this._handle, name, context.context ?? context);
+      }
+    }
+  } catch (e) {
+    // _handle is a Bun.listen SocketListener: it exposes stop(), not close().
+    this._handle.stop(true);
+    this._handle = null;
+    throw e;
   }
 
   // Unref the handle if the server was unref'ed prior to listening
@@ -4336,8 +4336,8 @@ function listenInCluster(
           onListen,
           sharedFd,
         );
-        handle.adopted = true;
       } catch (err) {
+        // With `handle.adopted` set by kRealListen, close() releases the key but not the fd.
         server[kClusterHandle] = null;
         server[kClusterUnixPath] = undefined;
         handle[kClusterOwner] = null;
diff --git a/test/js/node/cluster.test.ts b/test/js/node/cluster.test.ts
index 3248646bd3b0..e08180b02327 100644
--- a/test/js/node/cluster.test.ts
+++ b/test/js/node/cluster.test.ts
@@ -853,6 +853,69 @@ if (cluster.isPrimary) {
   expect(stdout).toContain("reply: echo:hi");
 }, 30_000);
 
+test("TLS cluster worker state matches the event that ends listen(): 'listening' or 'error'", async () => {
+  const dir = tempDirWithFiles("bun-test", {
+    "cert.pem": tlsCerts.cert,
+    "key.pem": tlsCerts.key,
+    "main.ts": `
+const cluster = require("node:cluster");
+const tls = require("node:tls");
+const fs = require("node:fs");
+const path = require("node:path");
+const key = fs.readFileSync(path.join(__dirname, "key.pem"));
+const cert = fs.readFileSync(path.join(__dirname, "cert.pem"));
+
+if (cluster.isPrimary) {
+  const worker = cluster.fork();
+  worker.on("message", msg => console.log("state:", JSON.stringify(msg)));
+  cluster.on("listening", (w, address) => {
+    const c = tls.connect({ port: address.port, host: "127.0.0.1", rejectUnauthorized: false });
+    c.setEncoding("utf8");
+    c.on("data", d => {
+      console.log("reply:", d);
+      c.end();
+      worker.kill();
+      process.exit(0);
+    });
+    c.on("error", e => {
+      console.log("client error:", e.code);
+      process.exit(1);
+    });
+  });
+} else {
+  const onConnection = socket => socket.end("ok");
+  const first = tls.createServer({ key, cert }, onConnection);
+  // Bun rejects the second name when it loads the entries into the listener
+  // that adopted the shared fd (#43092). Node accepts both.
+  const name = "a.b.c.d.e.f.g.h.i.j.k.example";
+  first.addContext(name, { key, cert });
+  first.addContext(name + ".", { key, cert });
+  const report = outcome =>
+    process.send({
+      outcome,
+      listening: first.listening,
+      hasAddress: first.address() !== null,
+      hasHandle: first._handle != null,
+    });
+  first.on("listening", () => report("listening"));
+  first.on("error", () => {
+    report("error");
+    // The worker's cluster state is still usable after the failure.
+    tls.createServer({ key, cert }, onConnection).listen(0);
+  });
+  first.listen(0);
+}
+`,
+  });
+  const { stdout } = await bunRun(joinP(dir, "main.ts"), bunEnv);
+  const state = stdout.match(/^state: (.*)$/m)?.[1];
+  expect([
+    '{"outcome":"listening","listening":true,"hasAddress":true,"hasHandle":true}',
+    '{"outcome":"error","listening":false,"hasAddress":false,"hasHandle":false}',
+  ]).toContain(state);
+  expect(stdout).toContain("reply: ok");
+}, 30_000);
+
 test("plain worker listening on a key already owned by a TLS shared-only handle fails with EINVAL", async () => {
   const dir = tempDirWithFiles("bun-test", {
     "cert.pem": tlsCerts.cert,
diff --git a/test/js/node/tls/node-tls-server.test.ts b/test/js/node/tls/node-tls-server.test.ts
index a672381930ae..87b6314b80c4 100644
--- a/test/js/node/tls/node-tls-server.test.ts
+++ b/test/js/node/tls/node-tls-server.test.ts
@@ -1437,6 +1437,38 @@ it("an asynchronous SNICallback resolving cb(null, null) still honors addContext
   await once(server, "close");
 });
 
+it("the server state matches the event that ends listen(): 'listening' or 'error'", async () => {
+  // Bun loads the addContext() entries into the native listener after the
+  // bind, and rejects the second of these two names there (#43092). Node
+  // accepts both and emits 'listening'. After either event the server state
+  // has to match it: a failed listen() leaves the server closed, as in Node.
+  const altCert = { key: rawKey, cert: cert };
+  const server: Server = createServer(COMMON_CERT, socket => socket.end());
+  const name = "a.b.c.d.e.f.g.h.i.j.k.example";
+  server.addContext(name, altCert);
+  server.addContext(name + ".", altCert);
+  server.listen(0, "127.0.0.1");
+  const outcome = await new Promise<string>(resolve => {
+    server.once("listening", () => resolve("listening"));
+    server.once("error", () => resolve("error"));
+  });
+  const state = {
+    outcome,
+    listening: server.listening,
+    hasAddress: server.address() !== null,
+    hasHandle: (server as any)._handle != null,
+  };
+  if (outcome === "listening") {
+    expect(state).toEqual({ outcome: "listening", listening: true, hasAddress: true, hasHandle: true });
+    server.close();
+    await once(server, "close");
+  } else {
+    expect(state).toEqual({ outcome: "error", listening: false, hasAddress: false, hasHandle: false });
+    const closeErr = await new Promise<any>(resolve => server.close(resolve));
+    expect(closeErr.code).toBe("ERR_SERVER_NOT_RUNNING");
+  }
+});
+
 describe("tls.Server socket destroySoon", () => {
   // destroySoon() after end(big) must deliver every byte even when the TLS write
   // batcher's final flush spills (#31584). The spill/kernel-buffer race hits ~4% of