diff --git a/BTCPayServer.Tests/UnitTest1.cs b/BTCPayServer.Tests/UnitTest1.cs
index 4599f9405..96c51a92f 100644
--- a/BTCPayServer.Tests/UnitTest1.cs
+++ b/BTCPayServer.Tests/UnitTest1.cs
@@ -897,6 +897,14 @@ namespace BTCPayServer.Tests
             {
                 await tester.StartAsync();
                 var proxy = tester.PayTester.GetService<Socks5HttpProxyServer>();
+                void AssertConnectionDropped()
+                {
+                    TestUtils.Eventually(() =>
+                    {
+                        Thread.MemoryBarrier();
+                        Assert.Equal(0, proxy.ConnectionCount);
+                    });
+                }
                 var httpFactory = tester.PayTester.GetService<IHttpClientFactory>();
                 var client = httpFactory.CreateClient(PayjoinClient.PayjoinOnionNamedClient);
                 Assert.NotNull(client);
@@ -905,46 +913,32 @@ namespace BTCPayServer.Tests
                 var result = await response.Content.ReadAsStringAsync();
                 Assert.DoesNotContain("You are not using Tor.", result);
                 Assert.Contains("Congratulations. This browser is configured to use Tor.", result);
-                Logs.Tester.LogInformation("Now we should have one connection");
-                TestUtils.Eventually(() =>
-                {
-                    Thread.MemoryBarrier();
-                    Assert.Equal(1, proxy.ConnectionCount);
-                });
+                AssertConnectionDropped();
                 response = await client.GetAsync("http://explorerzydxu5ecjrkwceayqybizmpjjznk5izmitf2modhcusuqlid.onion/");
                 response.EnsureSuccessStatusCode();
                 result = await response.Content.ReadAsStringAsync();
                 Assert.Contains("Bitcoin", result);
-                Logs.Tester.LogInformation("Now we should have two connections");
-                TestUtils.Eventually(() =>
-                {
-                    Thread.MemoryBarrier();
-                    Assert.Equal(2, proxy.ConnectionCount);
-                });
+
+                AssertConnectionDropped();
                 response = await client.GetAsync("http://explorerzydxu5ecjrkwceayqybizmpjjznk5izmitf2modhcusuqlid.onion/");
                 response.EnsureSuccessStatusCode();
-                Logs.Tester.LogInformation("Querying the same address should not create additional connection");
-                TestUtils.Eventually(() =>
-                {
-                    Thread.MemoryBarrier();
-                    Assert.Equal(2, proxy.ConnectionCount);
-                });
+                AssertConnectionDropped();
                 client.Dispose();
-                Logs.Tester.LogInformation("Disposing a HttpClient should not proxy connection");
-                TestUtils.Eventually(() =>
-                {
-                    Thread.MemoryBarrier();
-                    Assert.Equal(2, proxy.ConnectionCount);
-                });
+                AssertConnectionDropped();
                 client = httpFactory.CreateClient(PayjoinClient.PayjoinOnionNamedClient);
                 response = await client.GetAsync("http://explorerzydxu5ecjrkwceayqybizmpjjznk5izmitf2modhcusuqlid.onion/");
                 response.EnsureSuccessStatusCode();
-                Logs.Tester.LogInformation("Querying the same address with same client should not create additional connection");
-                TestUtils.Eventually(() =>
-                {
-                    Thread.MemoryBarrier();
-                    Assert.Equal(2, proxy.ConnectionCount);
-                });
+                AssertConnectionDropped();
+
+                Logs.Tester.LogInformation("Querying an onion address which can't be found should send http 500");
+                response = await client.GetAsync("http://dwoduwoi.onion/");
+                Assert.Equal(HttpStatusCode.InternalServerError, response.StatusCode);
+                AssertConnectionDropped();
+
+                Logs.Tester.LogInformation("Querying valid onion but unreachable should send error 502");
+                response = await client.GetAsync("http://fastrcl5totos3vekjbqcmgpnias5qytxnaj7gpxtxhubdcnfrkapqad.onion/");
+                Assert.Equal(HttpStatusCode.BadGateway, response.StatusCode);
+                AssertConnectionDropped();
             }
         }
 
diff --git a/BTCPayServer/HostedServices/Socks5HttpProxyServer.cs b/BTCPayServer/HostedServices/Socks5HttpProxyServer.cs
index 05c27bb36..2e8713391 100644
--- a/BTCPayServer/HostedServices/Socks5HttpProxyServer.cs
+++ b/BTCPayServer/HostedServices/Socks5HttpProxyServer.cs
@@ -26,11 +26,13 @@ namespace BTCPayServer.HostedServices
             public Socket ClientSocket;
             public Socket SocksSocket;
             public CancellationToken CancellationToken;
+            public CancellationTokenSource CancellationTokenSource;
 
             public void Dispose()
             {
                 Socks5HttpProxyServer.Dispose(ClientSocket);
                 Socks5HttpProxyServer.Dispose(SocksSocket);
+                CancellationTokenSource.Dispose();
             }
         }
         private readonly BTCPayServerOptions _opts;
@@ -76,11 +78,13 @@ namespace BTCPayServer.HostedServices
                 return;
             }
             var toSocksProxy  = new Socket(AddressFamily.InterNetwork, SocketType.Stream, ProtocolType.Tcp);
+            var connectionCts = CancellationTokenSource.CreateLinkedTokenSource(_Cts.Token);
             toSocksProxy.BeginConnect(_opts.SocksEndpoint, ConnectToSocks, new ProxyConnection()
             {
                 ClientSocket = clientSocket,
                 SocksSocket = toSocksProxy,
-                CancellationToken = _Cts.Token
+                CancellationToken = connectionCts.Token,
+                CancellationTokenSource = connectionCts 
             });
             _ServerSocket.BeginAccept(Accept, null);
         }
@@ -99,14 +103,17 @@ namespace BTCPayServer.HostedServices
             }
             Interlocked.Increment(ref connectionCount);
             var pipe = new Pipe(PipeOptions.Default);
-            var reading = FillPipeAsync(connection.ClientSocket, pipe.Writer, connection.CancellationToken);
-            var writing = ReadPipeAsync(connection.SocksSocket, connection.ClientSocket, pipe.Reader, connection.CancellationToken);
+            CancellationTokenSource.CreateLinkedTokenSource(connection.CancellationToken);
+            var reading = FillPipeAsync(connection.ClientSocket, pipe.Writer, connection.CancellationToken)
+                .ContinueWith(_ => connection.CancellationTokenSource.Cancel(), TaskScheduler.Default);
+            var writing = ReadPipeAsync(connection.SocksSocket, connection.ClientSocket, pipe.Reader, connection.CancellationToken)
+                .ContinueWith(_ => connection.CancellationTokenSource.Cancel(), TaskScheduler.Default);
             _ = Task.WhenAll(reading, writing)
                 .ContinueWith(_ =>
                 {
                     connection.Dispose();
                     Interlocked.Decrement(ref connectionCount);
-                });
+                }, TaskScheduler.Default);
         }
 
         private int connectionCount = 0;
@@ -197,19 +204,23 @@ namespace BTCPayServer.HostedServices
                     }
                     catch (SocksException e) when (e.SocksErrorCode == SocksErrorCode.HostUnreachable || e.SocksErrorCode == SocksErrorCode.HostUnreachable)
                     {
-                        await SendAsync(clientSocket , $"{httpVersion} 502 Bad Gateway\r\n\r\n", cancellationToken);
+                        await SendAsync(clientSocket , $"{httpVersion} 502 Bad Gateway\r\nContent-Length: 0\r\n\r\n", cancellationToken);
+                        goto done;
                     }
                     catch (SocksException e)
                     {
-                        await SendAsync(clientSocket , $"{httpVersion} 500 Internal Server Error\r\nX-Proxy-Error-Type: Socks {e.SocksErrorCode}\r\n\r\n", cancellationToken);
+                        await SendAsync(clientSocket , $"{httpVersion} 500 Internal Server Error\r\nContent-Length: 0\r\nX-Proxy-Error-Type: Socks {e.SocksErrorCode}\r\n\r\n", cancellationToken);
+                        goto done;
                     }
                     catch (SocketException e)
                     {
-                        await SendAsync(clientSocket , $"{httpVersion} 500 Internal Server Error\r\nX-Proxy-Error-Type: Socket {e.SocketErrorCode}\r\n\r\n", cancellationToken);
+                        await SendAsync(clientSocket , $"{httpVersion} 500 Internal Server Error\r\nContent-Length: 0\r\nX-Proxy-Error-Type: Socket {e.SocketErrorCode}\r\n\r\n", cancellationToken);
+                        goto done;
                     }
                     catch
                     {
                         await SendAsync(clientSocket , $"{httpVersion} 500 Internal Server Error\r\n\r\n", cancellationToken);
+                        goto done;
                     }
                 }
                 else
@@ -231,6 +242,7 @@ namespace BTCPayServer.HostedServices
                 }
             }
 
+            done:
             // Mark the PipeReader as complete
             reader.Complete();
         }
diff --git a/BTCPayServer/Payments/PayJoin/PayJoinExtensions.cs b/BTCPayServer/Payments/PayJoin/PayJoinExtensions.cs
index c1dc8cbe2..f67499e7a 100644
--- a/BTCPayServer/Payments/PayJoin/PayJoinExtensions.cs
+++ b/BTCPayServer/Payments/PayJoin/PayJoinExtensions.cs
@@ -17,6 +17,7 @@ namespace BTCPayServer.Payments.PayJoin
             services.AddSingleton<PayjoinClient>();
             services.AddTransient<Socks5HttpClientHandler>();
             services.AddHttpClient(PayjoinClient.PayjoinOnionNamedClient)
+                .ConfigureHttpClient(h => h.DefaultRequestHeaders.ConnectionClose = true )
                 .ConfigurePrimaryHttpMessageHandler<Socks5HttpClientHandler>();
         }
     }