diff --git a/src/bun.js/bindings/NodeHTTP.cpp b/src/bun.js/bindings/NodeHTTP.cpp
index 963745ed05..3a16e75f42 100644
--- a/src/bun.js/bindings/NodeHTTP.cpp
+++ b/src/bun.js/bindings/NodeHTTP.cpp
@@ -1037,6 +1037,11 @@ static void writeFetchHeadersToUWSResponse(WebCore::FetchHeaders& headers, uWS::
                 res->writeMark();
             }
         }
+
+        // Prevent automatic Date header insertion when user provides one
+        if (header.key == WebCore::HTTPHeaderName::Date) {
+            data->state |= uWS::HttpResponseData<isSSL>::HTTP_WROTE_DATE_HEADER;
+        }
         writeResponseHeader<isSSL>(res, name, value);
     }
 
diff --git a/test/regression/issue/21677.test.ts b/test/regression/issue/21677.test.ts
new file mode 100644
index 0000000000..b822a01902
--- /dev/null
+++ b/test/regression/issue/21677.test.ts
@@ -0,0 +1,100 @@
+import { expect, test } from "bun:test";
+
+test("issue #21677 - should not add redundant Date headers", async () => {
+  const testDate1 = new Date("2025-08-07T17:01:47.000Z").toUTCString();
+  const testDate2 = new Date("2025-08-07T17:02:23.000Z").toUTCString();
+  const testDate3 = new Date("2025-08-07T17:03:06.000Z").toUTCString();
+
+  using server = Bun.serve({
+    port: 0,
+    routes: {
+      "/static": () =>
+        new Response(`date test`, {
+          headers: { date: testDate1 },
+        }),
+      "/proxy": async () => {
+        // Create a simple server response with a Date header to proxy
+        const simpleResponse = new Response("proxied content", {
+          headers: {
+            "Date": testDate3,
+            "Content-Type": "text/plain",
+          },
+        });
+        return simpleResponse;
+      },
+    },
+    fetch: () =>
+      new Response(`date test`, {
+        headers: { date: testDate2 },
+      }),
+  });
+
+  // Test dynamic route (default fetch handler)
+  {
+    const response = await fetch(server.url);
+
+    // Should only have one Date header, not multiple
+    const dateHeaders = [...response.headers.entries()].filter(([key]) => key.toLowerCase() === "date");
+    expect(dateHeaders).toHaveLength(1);
+    expect(dateHeaders[0][1]).toBe(testDate2);
+  }
+
+  // Test static route
+  {
+    const response = await fetch(new URL("/static", server.url));
+
+    // Should only have one Date header, not multiple
+    const dateHeaders = [...response.headers.entries()].filter(([key]) => key.toLowerCase() === "date");
+    expect(dateHeaders).toHaveLength(1);
+    expect(dateHeaders[0][1]).toBe(testDate1);
+  }
+
+  // Test proxy route
+  {
+    const response = await fetch(new URL("/proxy", server.url));
+
+    // Should only have one Date header, not multiple
+    const dateHeaders = [...response.headers.entries()].filter(([key]) => key.toLowerCase() === "date");
+    expect(dateHeaders).toHaveLength(1);
+    expect(dateHeaders[0][1]).toBe(testDate3);
+  }
+});
+
+test("issue #21677 - reproduce with raw HTTP to verify duplicate headers", async () => {
+  const testDate = new Date("2025-08-07T17:02:23.000Z").toUTCString();
+
+  using server = Bun.serve({
+    port: 0,
+    fetch: () =>
+      new Response(`date test`, {
+        headers: { date: testDate },
+      }),
+  });
+
+  // Use TCP socket to get raw HTTP response and check for duplicate headers
+  await new Promise((resolve, reject) => {
+    const socket = Bun.connect({
+      hostname: "localhost",
+      port: server.port,
+      socket: {
+        data(socket, data) {
+          const response = data.toString();
+          // Should NOT contain multiple Date headers
+          const lines = response.split("\r\n");
+          const dateHeaderLines = lines.filter(line => line.toLowerCase().startsWith("date:"));
+
+          expect(dateHeaderLines).toHaveLength(1);
+          expect(dateHeaderLines[0]).toBe(`Date: ${testDate}`);
+          socket.end();
+          resolve(undefined);
+        },
+        error(socket, error) {
+          reject(error);
+        },
+        open(socket) {
+          socket.write("GET / HTTP/1.1\r\nHost: localhost\r\nConnection: close\r\n\r\n");
+        },
+      },
+    });
+  });
+});