diff --git a/src/runtime/server/server.zig b/src/runtime/server/server.zig
index a860f5640e9..54a7e85fd0f 100644
--- a/src/runtime/server/server.zig
+++ b/src/runtime/server/server.zig
@@ -2170,7 +2170,7 @@ pub fn NewServer(protocol_enum: enum { http, https }, development_kind: enum { d
                         if (!node_response.flags.upgraded and node_response.raw_response != null) {
                             const raw_response = node_response.raw_response.?;
                             if (!node_response.flags.request_has_completed and raw_response.state().isResponsePending()) {
-                                if (raw_response.state().isHttpStatusCalled()) {
+                                if (!raw_response.state().isHttpStatusCalled()) {
                                     raw_response.writeStatus("500 Internal Server Error");
                                     raw_response.endWithoutBody(true);
                                 } else {
diff --git a/test/js/node/http/node-http-sync-throw-500.test.ts b/test/js/node/http/node-http-sync-throw-500.test.ts
new file mode 100644
index 00000000000..139fb1c9f5f
--- /dev/null
+++ b/test/js/node/http/node-http-sync-throw-500.test.ts
@@ -0,0 +1,100 @@
+import { expect, test } from "bun:test";
+import { bunEnv, bunExe } from "harness";
+
+// When a node:http request handler throws synchronously before any status line
+// has been written, Bun should respond with 500 Internal Server Error rather
+// than defaulting to 200 OK. The cleanup path in server.zig checks whether a
+// status has already been sent via isHttpStatusCalled(); previously the
+// condition was inverted so the 500 branch was unreachable and endStream()
+// wrote a default "HTTP/1.1 200 OK".
+test.concurrent("node:http responds 500 when handler throws synchronously before writing status", async () => {
+  const script = /* js */ `
+    const http = require("node:http");
+    const net = require("node:net");
+    const { once } = require("node:events");
+
+    // Swallow the propagated handler exception so the process stays alive.
+    process.on("uncaughtException", err => {
+      process.stderr.write("uncaughtException:" + err.message + "\\n");
+    });
+
+    const server = http.createServer((req, res) => {
+      throw new Error("boom");
+    });
+
+    server.listen(0, "127.0.0.1", async () => {
+      const port = server.address().port;
+      const socket = net.connect(port, "127.0.0.1");
+      await once(socket, "connect");
+      socket.write("GET / HTTP/1.1\\r\\nHost: 127.0.0.1\\r\\nConnection: close\\r\\n\\r\\n");
+      let raw = "";
+      for await (const chunk of socket) raw += chunk.toString("latin1");
+      const statusLine = raw.slice(0, raw.indexOf("\\r\\n"));
+      process.stdout.write("STATUS_LINE:" + statusLine + "\\n");
+      server.close();
+      process.exit(0);
+    });
+  `;
+
+  await using proc = Bun.spawn({
+    cmd: [bunExe(), "-e", script],
+    env: bunEnv,
+    stdout: "pipe",
+    stderr: "pipe",
+    stdin: "ignore",
+  });
+
+  const [stdout, stderr, exitCode] = await Promise.all([proc.stdout.text(), proc.stderr.text(), proc.exited]);
+
+  expect(stderr).toContain("uncaughtException:boom");
+  expect(stdout.trim()).toBe("STATUS_LINE:HTTP/1.1 500 Internal Server Error");
+  expect(exitCode).toBe(0);
+});
+
+test.concurrent("node:http still terminates the response when handler throws after writeHead", async () => {
+  const script = /* js */ `
+    const http = require("node:http");
+    const net = require("node:net");
+    const { once } = require("node:events");
+
+    process.on("uncaughtException", err => {
+      process.stderr.write("uncaughtException:" + err.message + "\\n");
+    });
+
+    const server = http.createServer((req, res) => {
+      res.writeHead(201, { "x-before-throw": "yes" });
+      res.flushHeaders();
+      throw new Error("boom-after-head");
+    });
+
+    server.listen(0, "127.0.0.1", async () => {
+      const port = server.address().port;
+      const socket = net.connect(port, "127.0.0.1");
+      await once(socket, "connect");
+      socket.write("GET / HTTP/1.1\\r\\nHost: 127.0.0.1\\r\\nConnection: close\\r\\n\\r\\n");
+      let raw = "";
+      for await (const chunk of socket) raw += chunk.toString("latin1");
+      const statusLine = raw.slice(0, raw.indexOf("\\r\\n"));
+      process.stdout.write("STATUS_LINE:" + statusLine + "\\n");
+      process.stdout.write("HAS_HEADER:" + raw.includes("x-before-throw: yes") + "\\n");
+      server.close();
+      process.exit(0);
+    });
+  `;
+
+  await using proc = Bun.spawn({
+    cmd: [bunExe(), "-e", script],
+    env: bunEnv,
+    stdout: "pipe",
+    stderr: "pipe",
+    stdin: "ignore",
+  });
+
+  const [stdout, stderr, exitCode] = await Promise.all([proc.stdout.text(), proc.stderr.text(), proc.exited]);
+
+  expect(stderr).toContain("uncaughtException:boom-after-head");
+  // Status was already sent before the throw, so it stays 201, but the
+  // connection must still be terminated (we received a complete response).
+  expect(stdout.trim()).toBe("STATUS_LINE:HTTP/1.1 201 Created\nHAS_HEADER:true");
+  expect(exitCode).toBe(0);
+});