diff --git a/packages/bun-uws/src/HttpResponse.h b/packages/bun-uws/src/HttpResponse.h
index 03c82ca77d..a4b85a2053 100644
--- a/packages/bun-uws/src/HttpResponse.h
+++ b/packages/bun-uws/src/HttpResponse.h
@@ -125,6 +125,10 @@ public:
             }
         }
 
+        if (httpResponseData->state & HttpResponseData<SSL>::HTTP_WROTE_TRANSFER_ENCODING_HEADER) {
+            allowContentLength = false;
+        }
+
         /* if write was called and there was previously no Content-Length header set */
         if (httpResponseData->state & HttpResponseData<SSL>::HTTP_WRITE_CALLED && !(httpResponseData->state & HttpResponseData<SSL>::HTTP_WROTE_CONTENT_LENGTH_HEADER) && !httpResponseData->fromAncientRequest) {
 
diff --git a/packages/bun-uws/src/HttpResponseData.h b/packages/bun-uws/src/HttpResponseData.h
index 26c3428049..1870cdb69c 100644
--- a/packages/bun-uws/src/HttpResponseData.h
+++ b/packages/bun-uws/src/HttpResponseData.h
@@ -87,6 +87,7 @@ struct HttpResponseData : AsyncSocketData<SSL>, HttpParser {
         HTTP_CONNECTION_CLOSE = 16, // used
         HTTP_WROTE_CONTENT_LENGTH_HEADER = 32, // used
         HTTP_WROTE_DATE_HEADER = 64, // used
+        HTTP_WROTE_TRANSFER_ENCODING_HEADER = 128, // used
     };
 
     /* Shared context pointer */
diff --git a/src/bun.js/bindings/NodeHTTP.cpp b/src/bun.js/bindings/NodeHTTP.cpp
index 29eca691c0..4e31e65867 100644
--- a/src/bun.js/bindings/NodeHTTP.cpp
+++ b/src/bun.js/bindings/NodeHTTP.cpp
@@ -1038,6 +1038,11 @@ static void writeFetchHeadersToUWSResponse(WebCore::FetchHeaders& headers, uWS::
             }
         }
 
+        // Prevent automatic Date header insertion when user provides one
+        if (header.key == WebCore::HTTPHeaderName::TransferEncoding) {
+            data->state |= uWS::HttpResponseData<isSSL>::HTTP_WROTE_TRANSFER_ENCODING_HEADER;
+        }
+
         // Prevent automatic Date header insertion when user provides one
         if (header.key == WebCore::HTTPHeaderName::Date) {
             data->state |= uWS::HttpResponseData<isSSL>::HTTP_WROTE_DATE_HEADER;