diff --git a/src/ReverseProxy/Forwarder/HttpForwarder.cs b/src/ReverseProxy/Forwarder/HttpForwarder.cs
index 66880c895..ef3f03587 100644
--- a/src/ReverseProxy/Forwarder/HttpForwarder.cs
+++ b/src/ReverseProxy/Forwarder/HttpForwarder.cs
@@ -456,13 +456,18 @@ private async ValueTask<ForwarderError> HandleRequestFailureAsync(HttpContext co
     {
         if (requestException is OperationCanceledException)
         {
-            if (!context.RequestAborted.IsCancellationRequested && requestCancellationSource.IsCancellationRequested)
+            if (context.RequestAborted.IsCancellationRequested)
             {
-                return await ReportErrorAsync(ForwarderError.RequestTimedOut, StatusCodes.Status504GatewayTimeout);
+                return await ReportErrorAsync(ForwarderError.RequestCanceled, StatusCodes.Status502BadGateway);
             }
             else
             {
-                return await ReportErrorAsync(ForwarderError.RequestCanceled, StatusCodes.Status502BadGateway);
+#if NET6_0_OR_GREATER
+                Debug.Assert(requestCancellationSource.IsCancellationRequested || requestException.ToString().Contains("ConnectTimeout"), requestException.ToString());
+#else
+                Debug.Assert(requestCancellationSource.IsCancellationRequested || requestException.ToString().Contains("ConnectHelper"), requestException.ToString());
+#endif
+                return await ReportErrorAsync(ForwarderError.RequestTimedOut, StatusCodes.Status504GatewayTimeout);
             }
         }
 
diff --git a/test/ReverseProxy.Tests/Forwarder/HttpForwarderTests.cs b/test/ReverseProxy.Tests/Forwarder/HttpForwarderTests.cs
index c1f9fd8d9..e1fa6ce89 100644
--- a/test/ReverseProxy.Tests/Forwarder/HttpForwarderTests.cs
+++ b/test/ReverseProxy.Tests/Forwarder/HttpForwarderTests.cs
@@ -1360,6 +1360,40 @@ public async Task RequestTimedOut_Returns504()
         events.AssertContainProxyStages(new[] { ForwarderStage.SendAsyncStart });
     }
 
+    [Fact]
+    public async Task RequestConnectTimedOut_Returns504()
+    {
+        var events = TestEventListener.Collect();
+
+        var httpContext = new DefaultHttpContext();
+        httpContext.Request.Method = "GET";
+        httpContext.Request.Host = new HostString("example.com:3456");
+
+        var proxyResponseStream = new MemoryStream();
+        httpContext.Response.Body = proxyResponseStream;
+
+        var destinationPrefix = "https://microsoft.com:123/"; // Port that doesn't accept connections
+        var sut = CreateProxy();
+
+        using var client = new HttpMessageInvoker(new SocketsHttpHandler
+        {
+            // Time out immediately
+            ConnectTimeout = TimeSpan.FromTicks(1)
+        });
+
+        var proxyError = await sut.SendAsync(httpContext, destinationPrefix, client);
+
+        Assert.Equal(ForwarderError.RequestTimedOut, proxyError);
+        Assert.Equal(StatusCodes.Status504GatewayTimeout, httpContext.Response.StatusCode);
+        Assert.Equal(0, proxyResponseStream.Length);
+        var errorFeature = httpContext.Features.Get<IForwarderErrorFeature>();
+        Assert.Equal(ForwarderError.RequestTimedOut, errorFeature.Error);
+        Assert.IsAssignableFrom<OperationCanceledException>(errorFeature.Exception);
+
+        AssertProxyStartFailedStop(events, destinationPrefix, httpContext.Response.StatusCode, errorFeature.Error);
+        events.AssertContainProxyStages(new[] { ForwarderStage.SendAsyncStart });
+    }
+
     [Fact]
     public async Task RequestCanceled_Returns502()
     {