diff --git a/src/server.ts b/src/server.ts
index 8c13afd..aed7cef 100644
--- a/src/server.ts
+++ b/src/server.ts
@@ -208,7 +208,7 @@ function _createProxyFn<
     }
 
     let _resolve!: () => void;
-    let _reject: (error: any) => void;
+    let _reject!: (error: any) => void;
     const callbackPromise = new Promise<void>((resolve, reject) => {
       _resolve = resolve;
       _reject = reject;
@@ -222,24 +222,35 @@ function _createProxyFn<
     });
 
     for (const pass of server._getPasses(type)) {
-      const stop = pass(
-        req,
-        res,
-        requestOptions as ProxyServerOptions & { target: URL; forward: URL },
-        server as ProxyServer<
-          http.IncomingMessage | http2.Http2ServerRequest,
-          http.ServerResponse | http2.Http2ServerResponse
-        >,
-        head,
-        (error) => {
-          if (server.listenerCount("error") > 0) {
-            server.emit("error", error, req, res as ProxyServerRes | net.Socket);
-            _resolve();
-          } else {
-            _reject(error);
-          }
-        },
-      );
+      let stop: void | true;
+      try {
+        stop = pass(
+          req,
+          res,
+          requestOptions as ProxyServerOptions & { target: URL; forward: URL },
+          server as ProxyServer<
+            http.IncomingMessage | http2.Http2ServerRequest,
+            http.ServerResponse | http2.Http2ServerResponse
+          >,
+          head,
+          (error) => {
+            if (server.listenerCount("error") > 0) {
+              server.emit("error", error, req, res as ProxyServerRes | net.Socket);
+              _resolve();
+            } else {
+              _reject(error);
+            }
+          },
+        );
+      } catch (error) {
+        if (server.listenerCount("error") > 0) {
+          server.emit("error", error as Error, req, res as ProxyServerRes | net.Socket);
+          _resolve();
+        } else {
+          _reject(error);
+        }
+        break;
+      }
       // Passes can return a truthy value to halt the loop
       if (stop) {
         _resolve();
diff --git a/test/index.test.ts b/test/index.test.ts
index fcbca12..dc9e726 100644
--- a/test/index.test.ts
+++ b/test/index.test.ts
@@ -106,3 +106,144 @@ describe("httpxy", () => {
     expect(lastRejected).toBe(undefined);
   });
 });
+
+describe("middleware pass exceptions", () => {
+  it("should forward synchronous pass errors to error event", async () => {
+    const target = await new Promise<{
+      close: () => Promise<void>;
+      url: string;
+    }>((resolve, reject) => {
+      const server = http.createServer((_req, res) => {
+        res.end("ok");
+      });
+      server.once("error", reject);
+      server.listen(0, "127.0.0.1", () => {
+        const { port } = server.address() as AddressInfo;
+        resolve({
+          close: () =>
+            new Promise<void>((r, j) => {
+              server.close((e) => (e ? j(e) : r()));
+            }),
+          url: `http://127.0.0.1:${port}/`,
+        });
+      });
+    });
+
+    const proxy = createProxyServer({ target: target.url });
+
+    // Inject a middleware pass that throws synchronously (simulates ERR_INVALID_HTTP_TOKEN)
+    const testError = new TypeError("Invalid character in header");
+    proxy.before("web", "", () => {
+      throw testError;
+    });
+
+    const proxyServer = await new Promise<{
+      close: () => Promise<void>;
+      url: string;
+    }>((resolve, reject) => {
+      const server = http.createServer((req, res) => {
+        void proxy.web(req, res);
+      });
+      server.once("error", reject);
+      server.listen(0, "127.0.0.1", () => {
+        const { port } = server.address() as AddressInfo;
+        resolve({
+          close: () =>
+            new Promise<void>((r, j) => {
+              server.close((e) => (e ? j(e) : r()));
+            }),
+          url: `http://127.0.0.1:${port}/`,
+        });
+      });
+    });
+
+    try {
+      // With an error listener, the error should be emitted, not thrown
+      const errorPromise = new Promise<Error>((resolve) => {
+        proxy.on("error", (err, _req, res) => {
+          resolve(err);
+          // End the response so the request doesn't hang
+          if (res && "writeHead" in res && !res.headersSent) {
+            res.writeHead(502);
+            res.end();
+          }
+        });
+      });
+
+      // The request may fail since the proxy errored before sending a response
+      await $fetch(proxyServer.url, { ignoreResponseError: true }).catch(() => {});
+
+      const emittedError = await errorPromise;
+      expect(emittedError).toBe(testError);
+    } finally {
+      proxy.close();
+      await proxyServer.close();
+      await target.close();
+    }
+  });
+
+  it("should reject promise when no error listener and pass throws", async () => {
+    const target = await new Promise<{
+      close: () => Promise<void>;
+      url: string;
+    }>((resolve, reject) => {
+      const server = http.createServer((_req, res) => {
+        res.end("ok");
+      });
+      server.once("error", reject);
+      server.listen(0, "127.0.0.1", () => {
+        const { port } = server.address() as AddressInfo;
+        resolve({
+          close: () =>
+            new Promise<void>((r, j) => {
+              server.close((e) => (e ? j(e) : r()));
+            }),
+          url: `http://127.0.0.1:${port}/`,
+        });
+      });
+    });
+
+    const proxy = createProxyServer({ target: target.url });
+
+    // Inject a middleware pass that throws synchronously
+    const testError = new TypeError("Invalid character in header");
+    proxy.before("web", "", () => {
+      throw testError;
+    });
+
+    const proxyServer = await new Promise<{
+      close: () => Promise<void>;
+      url: string;
+    }>((resolve, reject) => {
+      const server = http.createServer((req, res) => {
+        void proxy.web(req, res).catch(() => {
+          res.statusCode = 502;
+          res.end("error");
+        });
+      });
+      server.once("error", reject);
+      server.listen(0, "127.0.0.1", () => {
+        const { port } = server.address() as AddressInfo;
+        resolve({
+          close: () =>
+            new Promise<void>((r, j) => {
+              server.close((e) => (e ? j(e) : r()));
+            }),
+          url: `http://127.0.0.1:${port}/`,
+        });
+      });
+    });
+
+    try {
+      // No error listener - the promise should reject with the thrown error
+      const response = await $fetch.raw(proxyServer.url, {
+        ignoreResponseError: true,
+      });
+      expect(response.status).toBe(502);
+    } finally {
+      proxy.close();
+      await proxyServer.close();
+      await target.close();
+    }
+  });
+});