diff --git a/src/libraries/System.Net.Http.WinHttpHandler/src/Resources/Strings.resx b/src/libraries/System.Net.Http.WinHttpHandler/src/Resources/Strings.resx
index 82e7445d67e742..5a6dd27e582283 100644
--- a/src/libraries/System.Net.Http.WinHttpHandler/src/Resources/Strings.resx
+++ b/src/libraries/System.Net.Http.WinHttpHandler/src/Resources/Strings.resx
@@ -135,4 +135,10 @@
   <data name="net_http_unsupported_version" xml:space="preserve">
     <value>Request version value must be one of 1.0, 1.1, 2.0, or 3.0.</value>
   </data>
+  <data name="net_http_headers_must_be_ascii" xml:space="preserve">
+    <value>Request headers must contain only ASCII characters.</value>
+  </data>
+  <data name="net_http_headers_invalid_chars" xml:space="preserve">
+    <value>Request headers must not contain CR, LF, or NUL characters.</value>
+  </data>
 </root>
diff --git a/src/libraries/System.Net.Http.WinHttpHandler/src/System/Net/Http/WinHttpHandler.cs b/src/libraries/System.Net.Http.WinHttpHandler/src/System/Net/Http/WinHttpHandler.cs
index 00617aee48378e..09d04cbe59b70f 100644
--- a/src/libraries/System.Net.Http.WinHttpHandler/src/System/Net/Http/WinHttpHandler.cs
+++ b/src/libraries/System.Net.Http.WinHttpHandler/src/System/Net/Http/WinHttpHandler.cs
@@ -709,6 +709,34 @@ private static WinHttpChunkMode GetChunkedModeForSend(HttpRequestMessage request
             return chunkedMode;
         }
 
+        private static bool IsValidHeaderChar(char c)
+        {
+            // Allow Latin-1 characters (0-255) but reject dangerous control characters
+            return c <= 255 && c != '\0' && c != '\r' && c != '\n';
+        }
+
+        private static void ValidateHeaderValues(System.Net.Http.Headers.HttpHeaders headers)
+        {
+            foreach (var header in headers)
+            {
+                foreach (var value in header.Value)
+                {
+                    ValidateHeaderValue(value);
+                }
+            }
+        }
+
+        private static void ValidateHeaderValue(string value)
+        {
+            for (int i = 0; i < value.Length; i++)
+            {
+                if (!IsValidHeaderChar(value[i]))
+                {
+                    throw new HttpRequestException(SR.net_http_headers_invalid_chars);
+                }
+            }
+        }
+
         private static void AddRequestHeaders(
             SafeWinHttpHandle requestHandle,
             HttpRequestMessage requestMessage,
@@ -734,14 +762,17 @@ private static void AddRequestHeaders(
                 string? cookieHeader = WinHttpCookieContainerAdapter.GetCookieHeader(requestMessage.RequestUri, cookies);
                 if (!string.IsNullOrEmpty(cookieHeader))
                 {
+                    ValidateHeaderValue(cookieHeader);
                     requestHeadersBuffer.AppendLine(cookieHeader);
                 }
             }
 
-            // Serialize general request headers.
-            requestHeadersBuffer.AppendLine(requestMessage.Headers.ToString());
+            // Validate and serialize general request headers
+            ValidateHeaderValues(requestMessage.Headers);
+            string generalHeaders = requestMessage.Headers.ToString();
+            requestHeadersBuffer.Append(generalHeaders);
 
-            // Serialize entity-body (content) headers.
+            // Serialize entity-body (content) headers and validate for ASCII.
             if (requestMessage.Content != null)
             {
                 // TODO https://github.com/dotnet/runtime/issues/16162:
@@ -754,7 +785,10 @@ private static void AddRequestHeaders(
                     requestMessage.Content.Headers.ContentLength = contentLength;
                 }
 
-                requestHeadersBuffer.AppendLine(requestMessage.Content.Headers.ToString());
+                // Validate and serialize entity-body (content) headers
+                ValidateHeaderValues(requestMessage.Content.Headers);
+                string contentHeaders = requestMessage.Content.Headers.ToString();
+                requestHeadersBuffer.Append(contentHeaders);
             }
 
             // Add request headers to WinHTTP request handle.
diff --git a/src/libraries/System.Net.Http.WinHttpHandler/tests/UnitTests/WinHttpHandlerTest.cs b/src/libraries/System.Net.Http.WinHttpHandler/tests/UnitTests/WinHttpHandlerTest.cs
index 15f7accca5d46f..91220735e6bf07 100644
--- a/src/libraries/System.Net.Http.WinHttpHandler/tests/UnitTests/WinHttpHandlerTest.cs
+++ b/src/libraries/System.Net.Http.WinHttpHandler/tests/UnitTests/WinHttpHandlerTest.cs
@@ -837,6 +837,107 @@ public void SendAsync_MultipleCallsWithDispose_NoHandleLeaksManuallyVerifiedUsin
             }
         }
 
+        [Fact]
+        public void SendAsync_RequestWithDangerousControlHeaderValue_ThrowsHttpRequestException()
+        {
+            using (var handler = new WinHttpHandler())
+            {
+                TestServer.SetResponse(DecompressionMethods.None, TestServer.ExpectedResponseBody);
+                
+                var invoker = new HttpMessageInvoker(handler, false);
+                var request = new HttpRequestMessage(HttpMethod.Get, TestServer.FakeServerEndpoint);
+                request.Headers.Add("Custom-Header", "HeaderValue\0WithNUL");
+                
+                var ex = Assert.Throws<HttpRequestException>(() =>
+                {
+                    Task<HttpResponseMessage> task = invoker.SendAsync(request, CancellationToken.None);
+                    task.GetAwaiter().GetResult();
+                });
+                
+                Assert.Contains("CR, LF, or NUL", ex.Message);
+            }
+        }
+
+        [Fact]
+        public void SendAsync_RequestWithLatin1HeaderValue_Succeeds()
+        {
+            using (var handler = new WinHttpHandler())
+            {
+                TestServer.SetResponse(DecompressionMethods.None, TestServer.ExpectedResponseBody);
+                
+                var invoker = new HttpMessageInvoker(handler, false);
+                var request = new HttpRequestMessage(HttpMethod.Get, TestServer.FakeServerEndpoint);
+                request.Headers.Add("Custom-Header", "HeaderValue\u00A9WithLatin1");
+                
+                Task<HttpResponseMessage> task = invoker.SendAsync(request, CancellationToken.None);
+                using (HttpResponseMessage response = task.GetAwaiter().GetResult())
+                {
+                    Assert.Equal(HttpStatusCode.OK, response.StatusCode);
+                }
+            }
+        }
+
+        [Fact] 
+        public void SendAsync_RequestWithAsciiHeaderValue_Succeeds()
+        {
+            using (var handler = new WinHttpHandler())
+            {
+                TestServer.SetResponse(DecompressionMethods.None, TestServer.ExpectedResponseBody);
+                
+                var invoker = new HttpMessageInvoker(handler, false);
+                var request = new HttpRequestMessage(HttpMethod.Get, TestServer.FakeServerEndpoint);
+                request.Headers.Add("Custom-Header", "ValidASCIIHeaderValue123");
+                
+                Task<HttpResponseMessage> task = invoker.SendAsync(request, CancellationToken.None);
+                using (HttpResponseMessage response = task.GetAwaiter().GetResult())
+                {
+                    Assert.Equal(HttpStatusCode.OK, response.StatusCode);
+                }
+            }
+        }
+
+        [Fact]
+        public void SendAsync_RequestWithDangerousControlContentHeader_ThrowsHttpRequestException()
+        {
+            using (var handler = new WinHttpHandler())
+            {
+                TestServer.SetResponse(DecompressionMethods.None, TestServer.ExpectedResponseBody);
+                
+                var invoker = new HttpMessageInvoker(handler, false);
+                var request = new HttpRequestMessage(HttpMethod.Post, TestServer.FakeServerEndpoint);
+                request.Content = new StringContent("test content");
+                request.Content.Headers.Add("Custom-Content-Header", "ContentValue\0WithNUL");
+                
+                var ex = Assert.Throws<HttpRequestException>(() =>
+                {
+                    Task<HttpResponseMessage> task = invoker.SendAsync(request, CancellationToken.None);
+                    task.GetAwaiter().GetResult();
+                });
+                
+                Assert.Contains("CR, LF, or NUL", ex.Message);
+            }
+        }
+
+        [Fact]
+        public void SendAsync_RequestWithLatin1ContentHeader_Succeeds()
+        {
+            using (var handler = new WinHttpHandler())
+            {
+                TestServer.SetResponse(DecompressionMethods.None, TestServer.ExpectedResponseBody);
+                
+                var invoker = new HttpMessageInvoker(handler, false);
+                var request = new HttpRequestMessage(HttpMethod.Post, TestServer.FakeServerEndpoint);
+                request.Content = new StringContent("test content");
+                request.Content.Headers.Add("Custom-Content-Header", "ContentValue\u00A9WithLatin1");
+                
+                Task<HttpResponseMessage> task = invoker.SendAsync(request, CancellationToken.None);
+                using (HttpResponseMessage response = task.GetAwaiter().GetResult())
+                {
+                    Assert.Equal(HttpStatusCode.OK, response.StatusCode);
+                }
+            }
+        }
+
         // Commented out as the test relies on finalizer for cleanup and only has value as written
         // when run on its own and manual analysis is done of logs.
         //[Fact]