diff --git a/src/js/node/_http_server.ts b/src/js/node/_http_server.ts
index ae646dcd41..d45cc321e3 100644
--- a/src/js/node/_http_server.ts
+++ b/src/js/node/_http_server.ts
@@ -1177,17 +1177,29 @@ function _writeHead(statusCode, reason, obj, response) {
         if (k) response.setHeader(k, obj[k]);
       }
     }
-    if (
-      (response.chunkedEncoding !== true || response.hasHeader("content-length")) &&
-      (response._trailer || response.hasHeader("trailer"))
-    ) {
-      // remove the invalid content-length or trailer header
-      if (hasContentLength) {
-        response.removeHeader("trailer");
-      } else {
-        response.removeHeader("content-length");
+    // Check if chunked encoding is being used. Trailers require chunked encoding.
+    // Check both the chunkedEncoding property and the Transfer-Encoding header.
+    const teHeader = response.getHeader("transfer-encoding");
+    const isChunked = response.chunkedEncoding === true || (teHeader && /chunked/i.test(String(teHeader)));
+    const hasContentLen = response.hasHeader("content-length");
+
+    if (!isChunked || hasContentLen) {
+      // Trailers cannot be used without chunked encoding
+      if (response.hasHeader("trailer")) {
+        // If "Trailer" header is explicitly set, that's an error
+        if (hasContentLength) {
+          response.removeHeader("trailer");
+        } else {
+          response.removeHeader("content-length");
+        }
+        throw $ERR_HTTP_TRAILER_INVALID("Trailers are invalid with this transfer encoding");
+      }
+      // If only _trailer is set (via addTrailers), silently discard per Node.js docs:
+      // "Trailers will only be emitted if chunked encoding is used for the response;
+      // if it is not (e.g. if the request was HTTP/1.0), they will be silently discarded."
+      if (response._trailer) {
+        response._trailer = "";
       }
-      throw $ERR_HTTP_TRAILER_INVALID("Trailers are invalid with this transfer encoding");
     }
   }
 
diff --git a/test/regression/issue/26171.test.ts b/test/regression/issue/26171.test.ts
new file mode 100644
index 0000000000..b2ba4799ac
--- /dev/null
+++ b/test/regression/issue/26171.test.ts
@@ -0,0 +1,120 @@
+import { expect, test } from "bun:test";
+
+// https://github.com/oven-sh/bun/issues/26171
+// res.addTrailers() before res.writeHead() and res.end() should silently discard
+// trailers when chunked encoding is not enabled, matching Node.js behavior.
+
+// Direct test using node:http server - this is the exact reproduction from the issue
+test("node:http server - addTrailers before writeHead should not throw", async () => {
+  const { createServer } = await import("node:http");
+
+  const server = createServer((req, res) => {
+    // Add trailers before writeHead - per Node.js docs, these should be silently discarded
+    // when chunked encoding is not used
+    res.addTrailers({ "Content-MD5": "7895bf4b8828b55ceaf47747b4bca667" });
+    res.writeHead(200);
+    res.end("OK");
+  });
+
+  await new Promise<void>(resolve => {
+    server.listen(0, () => resolve());
+  });
+
+  const port = (server.address() as any).port;
+
+  try {
+    const response = await fetch(`http://localhost:${port}`);
+    expect(response.status).toBe(200);
+    const text = await response.text();
+    expect(text).toBe("OK");
+  } finally {
+    server.close();
+  }
+});
+
+// Test with explicit Content-Length header
+test("node:http server - addTrailers with Content-Length should be silently discarded", async () => {
+  const { createServer } = await import("node:http");
+
+  const server = createServer((req, res) => {
+    // Add trailers before writeHead - per Node.js docs, these should be silently discarded
+    res.addTrailers({ "Content-MD5": "7895bf4b8828b55ceaf47747b4bca667" });
+    res.writeHead(200, { "Content-Length": "2" });
+    res.end("OK");
+  });
+
+  await new Promise<void>(resolve => {
+    server.listen(0, () => resolve());
+  });
+
+  const port = (server.address() as any).port;
+
+  try {
+    const response = await fetch(`http://localhost:${port}`);
+    expect(response.status).toBe(200);
+    const text = await response.text();
+    expect(text).toBe("OK");
+  } finally {
+    server.close();
+  }
+});
+
+// Test that trailers work correctly with chunked encoding
+test("node:http server - addTrailers with chunked encoding works", async () => {
+  const { createServer } = await import("node:http");
+
+  const server = createServer((req, res) => {
+    // When using chunked encoding (no Content-Length), trailers should work
+    res.writeHead(200, { "Transfer-Encoding": "chunked", "Trailer": "Content-MD5" });
+    res.write("Hello");
+    res.addTrailers({ "Content-MD5": "7895bf4b8828b55ceaf47747b4bca667" });
+    res.end();
+  });
+
+  await new Promise<void>(resolve => {
+    server.listen(0, () => resolve());
+  });
+
+  const port = (server.address() as any).port;
+
+  try {
+    const response = await fetch(`http://localhost:${port}`);
+    expect(response.status).toBe(200);
+    const text = await response.text();
+    expect(text).toBe("Hello");
+  } finally {
+    server.close();
+  }
+});
+
+// Test that explicit Trailer header without chunked encoding still throws
+test("node:http server - explicit Trailer header with Content-Length throws", async () => {
+  const { createServer } = await import("node:http");
+  let errorCode: string | null = null;
+
+  const server = createServer((req, res) => {
+    // Setting the Trailer header explicitly should throw when not using chunked encoding
+    try {
+      res.writeHead(200, { "Content-Length": "2", "Trailer": "Content-MD5" });
+      res.end("OK");
+    } catch (e: any) {
+      errorCode = e.code;
+      // Can't call writeHead again after it threw, so just destroy the socket
+      res.socket?.destroy();
+    }
+  });
+
+  await new Promise<void>(resolve => {
+    server.listen(0, () => resolve());
+  });
+
+  const port = (server.address() as any).port;
+
+  try {
+    await fetch(`http://localhost:${port}`).catch(() => {});
+    // The error should have been caught
+    expect(errorCode).toBe("ERR_HTTP_TRAILER_INVALID");
+  } finally {
+    server.close();
+  }
+});