diff --git a/eng/test-configuration.json b/eng/test-configuration.json
index adea26ddb23335..abbbdf47600543 100644
--- a/eng/test-configuration.json
+++ b/eng/test-configuration.json
@@ -3,7 +3,6 @@
   "defaultOnFailure": "fail",
   "localRerunCount": 2,
   "retryOnRules": [
-    { "testAssembly": { "wildcard": "System.Net.*" } },
     { "failureMessage": { "regex": ".*Timed out after .* waiting for the browser to be ready.*" } },
     { "failureMessage": { "regex": "System.IO.IOException : Process for .*chrome.*unexpectedly exited.* during startup" } }
   ]
diff --git a/src/libraries/System.Net.Http/tests/FunctionalTests/SocketsHttpHandlerTest.Cancellation.cs b/src/libraries/System.Net.Http/tests/FunctionalTests/SocketsHttpHandlerTest.Cancellation.cs
index ae1669c18e68b8..68646e95861fb0 100644
--- a/src/libraries/System.Net.Http/tests/FunctionalTests/SocketsHttpHandlerTest.Cancellation.cs
+++ b/src/libraries/System.Net.Http/tests/FunctionalTests/SocketsHttpHandlerTest.Cancellation.cs
@@ -4,12 +4,14 @@
 using System.Diagnostics;
 using System.IO;
 using System.Net.Sockets;
+using System.Linq;
 using System.Net.Test.Common;
 using System.Threading;
 using System.Threading.Tasks;
 using Microsoft.DotNet.RemoteExecutor;
 using Xunit;
 using Xunit.Abstractions;
+using TestUtilities;
 
 namespace System.Net.Http.Functional.Tests
 {
@@ -107,7 +109,21 @@ await LoopbackServerFactory.CreateClientAndServerAsync(async uri =>
             options: new GenericLoopbackOptions() { UseSsl = false });
         }
 
-        [OuterLoop]
+        [Fact] public async Task ConnectionFailure_AfterInitialRequestCancelled_SecondRequestSucceedsOnNewConnection2() => await ConnectionFailure_AfterInitialRequestCancelled_SecondRequestSucceedsOnNewConnection(true);
+        [Fact] public async Task ConnectionFailure_AfterInitialRequestCancelled_SecondRequestSucceedsOnNewConnection3() => await ConnectionFailure_AfterInitialRequestCancelled_SecondRequestSucceedsOnNewConnection(true);
+        [Fact] public async Task ConnectionFailure_AfterInitialRequestCancelled_SecondRequestSucceedsOnNewConnection4() => await ConnectionFailure_AfterInitialRequestCancelled_SecondRequestSucceedsOnNewConnection(true);
+        [Fact] public async Task ConnectionFailure_AfterInitialRequestCancelled_SecondRequestSucceedsOnNewConnection5() => await ConnectionFailure_AfterInitialRequestCancelled_SecondRequestSucceedsOnNewConnection(true);
+        [Fact] public async Task ConnectionFailure_AfterInitialRequestCancelled_SecondRequestSucceedsOnNewConnection6() => await ConnectionFailure_AfterInitialRequestCancelled_SecondRequestSucceedsOnNewConnection(true);
+        [Fact] public async Task ConnectionFailure_AfterInitialRequestCancelled_SecondRequestSucceedsOnNewConnection7() => await ConnectionFailure_AfterInitialRequestCancelled_SecondRequestSucceedsOnNewConnection(true);
+        [Fact] public async Task ConnectionFailure_AfterInitialRequestCancelled_SecondRequestSucceedsOnNewConnection8() => await ConnectionFailure_AfterInitialRequestCancelled_SecondRequestSucceedsOnNewConnection(true);
+        [Fact] public async Task ConnectionFailure_AfterInitialRequestCancelled_SecondRequestSucceedsOnNewConnection9() => await ConnectionFailure_AfterInitialRequestCancelled_SecondRequestSucceedsOnNewConnection(true);
+        [Fact] public async Task ConnectionFailure_AfterInitialRequestCancelled_SecondRequestSucceedsOnNewConnection10() => await ConnectionFailure_AfterInitialRequestCancelled_SecondRequestSucceedsOnNewConnection(true);
+        [Fact] public async Task ConnectionFailure_AfterInitialRequestCancelled_SecondRequestSucceedsOnNewConnection11() => await ConnectionFailure_AfterInitialRequestCancelled_SecondRequestSucceedsOnNewConnection(true);
+        [Fact] public async Task ConnectionFailure_AfterInitialRequestCancelled_SecondRequestSucceedsOnNewConnection12() => await ConnectionFailure_AfterInitialRequestCancelled_SecondRequestSucceedsOnNewConnection(true);
+        [Fact] public async Task ConnectionFailure_AfterInitialRequestCancelled_SecondRequestSucceedsOnNewConnection13() => await ConnectionFailure_AfterInitialRequestCancelled_SecondRequestSucceedsOnNewConnection(true);
+        [Fact] public async Task ConnectionFailure_AfterInitialRequestCancelled_SecondRequestSucceedsOnNewConnection14() => await ConnectionFailure_AfterInitialRequestCancelled_SecondRequestSucceedsOnNewConnection(true);
+        [Fact] public async Task ConnectionFailure_AfterInitialRequestCancelled_SecondRequestSucceedsOnNewConnection15() => await ConnectionFailure_AfterInitialRequestCancelled_SecondRequestSucceedsOnNewConnection(true);
+
         [Theory]
         [InlineData(true)]
         [InlineData(false)]
@@ -125,18 +141,19 @@ public async Task ConnectionFailure_AfterInitialRequestCancelled_SecondRequestSu
                 return;
             }
 
+            using var listener = new TestEventListener(_output, TestEventListener.NetworkingEvents);
+
             await LoopbackServerFactory.CreateClientAndServerAsync(async uri =>
             {
                 int connectCount = 0;
 
-                TaskCompletionSource tcsFirstConnectionInitiated = new TaskCompletionSource(TaskCreationOptions.RunContinuationsAsynchronously);
-                TaskCompletionSource tcsFirstRequestCanceled = new TaskCompletionSource(TaskCreationOptions.RunContinuationsAsynchronously);
+                var tcsFirstConnectionInitiated = new TaskCompletionSource(TaskCreationOptions.RunContinuationsAsynchronously);
+                var tcsFirstRequestCanceled = new TaskCompletionSource(TaskCreationOptions.RunContinuationsAsynchronously);
 
-                using (var handler = CreateHttpClientHandler(allowAllCertificates: true))
-                using (var client = CreateHttpClient(handler))
+                using (HttpClientHandler handler = CreateHttpClientHandler())
+                using (HttpClient client = CreateHttpClient(handler))
                 {
-                    var socketsHandler = GetUnderlyingSocketsHttpHandler(handler);
-                    socketsHandler.ConnectCallback = async (context, token) =>
+                    GetUnderlyingSocketsHttpHandler(handler).ConnectCallback = async (context, token) =>
                     {
                         // Note we force serialization of connection creation by waiting on tcsFirstConnectionInitiated below,
                         // so we don't need to worry about concurrent access to connectCount.
@@ -145,6 +162,8 @@ await LoopbackServerFactory.CreateClientAndServerAsync(async uri =>
 
                         Assert.True(connectCount <= 2);
 
+                        _output.WriteLine($"Connection count {connectCount}");
+
                         if (isFirstConnection)
                         {
                             tcsFirstConnectionInitiated.SetResult();
@@ -157,6 +176,8 @@ await LoopbackServerFactory.CreateClientAndServerAsync(async uri =>
                         // Wait until first request is cancelled and has completed
                         await tcsFirstRequestCanceled.Task;
 
+                        _output.WriteLine($"After tcsFirstRequestCanceled {isFirstConnection}");
+
                         if (isFirstConnection)
                         {
                             // Fail the first connection attempt
@@ -170,27 +191,34 @@ await LoopbackServerFactory.CreateClientAndServerAsync(async uri =>
                     };
 
                     using CancellationTokenSource cts = new CancellationTokenSource();
-                    Task<HttpResponseMessage> t1 = client.SendAsync(new HttpRequestMessage(HttpMethod.Get, uri) { Version = UseVersion, VersionPolicy = HttpVersionPolicy.RequestVersionExact }, cts.Token);
+                    Task<HttpResponseMessage> t1 = client.SendAsync(CreateRequest(HttpMethod.Get, uri, UseVersion, exactVersion: true), cts.Token);
+                    _output.WriteLine("t1");
 
                     // Wait for the connection attempt to be initiated before we send the second request, to avoid races in connection creation
-                    await tcsFirstConnectionInitiated.Task;
-                    Task<HttpResponseMessage> t2 = client.SendAsync(new HttpRequestMessage(HttpMethod.Get, uri) { Version = UseVersion, VersionPolicy = HttpVersionPolicy.RequestVersionExact }, default);
+                    await tcsFirstConnectionInitiated.Task.WaitAsync(TestHelper.PassingTestTimeout);
+                    Task<HttpResponseMessage> t2 = client.SendAsync(CreateRequest(HttpMethod.Get, uri, UseVersion, exactVersion: true), CancellationToken.None);
+                    _output.WriteLine("t2");
 
                     // Cancel the first message and wait for it to complete
                     cts.Cancel();
-                    await Assert.ThrowsAnyAsync<OperationCanceledException>(() => t1);
+                    await Assert.ThrowsAnyAsync<OperationCanceledException>(() => t1).WaitAsync(TestHelper.PassingTestTimeout);
+                    _output.WriteLine("ThrowsAnyAsync");
 
                     // Signal connections to proceed
                     tcsFirstRequestCanceled.SetResult();
 
                     // Second request should succeed, even though the first connection failed
-                    HttpResponseMessage resp2 = await t2;
+                    HttpResponseMessage resp2 = await t2.WaitAsync(TestHelper.PassingTestTimeout);
+                    _output.WriteLine("resp2");
                     Assert.Equal(HttpStatusCode.OK, resp2.StatusCode);
-                    Assert.Equal("Hello world", await resp2.Content.ReadAsStringAsync());
+                    Assert.Equal("Hello world", await resp2.Content.ReadAsStringAsync().WaitAsync(TestHelper.PassingTestTimeout));
+
+                    Assert.True(connectCount == 2);
                 }
             }, async server =>
             {
-                await server.AcceptConnectionSendResponseAndCloseAsync(content: "Hello world");
+                await server.HandleRequestAsync(content: "Hello world").WaitAsync(TestHelper.PassingTestTimeout);
+                _output.WriteLine("Server done");
             },
             options: new GenericLoopbackOptions() { UseSsl = useSsl });
         }