diff --git a/src/shared/Core.Tests/Commands/DiagnoseCommandTests.cs b/src/shared/Core.Tests/Commands/DiagnoseCommandTests.cs
new file mode 100644
index 000000000..0118e9d85
--- /dev/null
+++ b/src/shared/Core.Tests/Commands/DiagnoseCommandTests.cs
@@ -0,0 +1,82 @@
+using System;
+using System.Net.Http;
+using System.Security.AccessControl;
+using System.Text;
+using GitCredentialManager.Diagnostics;
+using GitCredentialManager.Tests.Objects;
+using Xunit;
+
+namespace Core.Tests.Commands;
+
+public class DiagnoseCommandTests
+{
+    [Fact]
+    public void NetworkingDiagnostic_SendHttpRequest_Primary_OK()
+    {
+        var primaryUriString = "http://example.com";
+        var sb = new StringBuilder();
+        var context = new TestCommandContext();
+        var networkingDiagnostic = new NetworkingDiagnostic(context);
+        var primaryUri = new Uri(primaryUriString);
+        var httpHandler = new TestHttpMessageHandler();
+        var httpResponse = new HttpResponseMessage();
+        var expected = $"Sending HEAD request to {primaryUriString}... OK{Environment.NewLine}";
+
+        httpHandler.Setup(HttpMethod.Head, primaryUri, httpResponse);
+
+        networkingDiagnostic.SendHttpRequest(sb, new HttpClient(httpHandler));
+
+        httpHandler.AssertRequest(HttpMethod.Head, primaryUri, expectedNumberOfCalls: 1);
+        Assert.Contains(expected, sb.ToString());
+    }
+
+    [Fact]
+    public void NetworkingDiagnostic_SendHttpRequest_Backup_OK()
+    {
+        var primaryUriString = "http://example.com";
+        var backupUriString = "http://httpforever.com";
+        var sb = new StringBuilder();
+        var context = new TestCommandContext();
+        var networkingDiagnostic = new NetworkingDiagnostic(context);
+        var primaryUri = new Uri(primaryUriString);
+        var backupUri = new Uri(backupUriString);
+        var httpHandler = new TestHttpMessageHandler { SimulatePrimaryUriFailure = true };
+        var httpResponse = new HttpResponseMessage();
+        var expected = $"Sending HEAD request to {primaryUriString}... warning: HEAD request failed{Environment.NewLine}" +
+                       $"Sending HEAD request to {backupUriString}... OK{Environment.NewLine}";
+
+        httpHandler.Setup(HttpMethod.Head, primaryUri, httpResponse);
+        httpHandler.Setup(HttpMethod.Head, backupUri, httpResponse);
+
+        networkingDiagnostic.SendHttpRequest(sb, new HttpClient(httpHandler));
+
+        httpHandler.AssertRequest(HttpMethod.Head, primaryUri, expectedNumberOfCalls: 1);
+        httpHandler.AssertRequest(HttpMethod.Head, backupUri, expectedNumberOfCalls: 1);
+        Assert.Contains(expected, sb.ToString());
+    }
+
+    [Fact]
+    public void NetworkingDiagnostic_SendHttpRequest_No_Network()
+    {
+        var primaryUriString = "http://example.com";
+        var backupUriString = "http://httpforever.com";
+        var sb = new StringBuilder();
+        var context = new TestCommandContext();
+        var networkingDiagnostic = new NetworkingDiagnostic(context);
+        var primaryUri = new Uri(primaryUriString);
+        var backupUri = new Uri(backupUriString);
+        var httpHandler = new TestHttpMessageHandler { SimulateNoNetwork = true };
+        var httpResponse = new HttpResponseMessage();
+        var expected = $"Sending HEAD request to {primaryUriString}... warning: HEAD request failed{Environment.NewLine}" +
+                       $"Sending HEAD request to {backupUriString}... warning: HEAD request failed{Environment.NewLine}";
+
+        httpHandler.Setup(HttpMethod.Head, primaryUri, httpResponse);
+        httpHandler.Setup(HttpMethod.Head, backupUri, httpResponse);
+
+        networkingDiagnostic.SendHttpRequest(sb, new HttpClient(httpHandler));
+
+        httpHandler.AssertRequest(HttpMethod.Head, primaryUri, expectedNumberOfCalls: 1);
+        httpHandler.AssertRequest(HttpMethod.Head, backupUri, expectedNumberOfCalls: 1);
+        Assert.Contains(expected, sb.ToString());
+    }
+}
diff --git a/src/shared/Core/Diagnostics/NetworkingDiagnostic.cs b/src/shared/Core/Diagnostics/NetworkingDiagnostic.cs
index 310b26361..50ab5b4da 100644
--- a/src/shared/Core/Diagnostics/NetworkingDiagnostic.cs
+++ b/src/shared/Core/Diagnostics/NetworkingDiagnostic.cs
@@ -12,6 +12,7 @@ namespace GitCredentialManager.Diagnostics
     public class NetworkingDiagnostic : Diagnostic
     {
         private const string TestHttpUri = "http://example.com";
+        private const string TestHttpUriFallback = "http://httpforever.com";
         private const string TestHttpsUri = "https://example.com";
 
         public NetworkingDiagnostic(ICommandContext commandContext)
@@ -28,9 +29,7 @@ protected override async Task<bool> RunInternalAsync(StringBuilder log, IList<st
             bool hasNetwork = NetworkInterface.GetIsNetworkAvailable();
             log.AppendLine($"IsNetworkAvailable: {hasNetwork}");
 
-            log.Append($"Sending HEAD request to {TestHttpUri}...");
-            using var httpResponse = await httpClient.HeadAsync(TestHttpUri);
-            log.AppendLine(" OK");
+            SendHttpRequest(log, httpClient);
 
             log.Append($"Sending HEAD request to {TestHttpsUri}...");
             using var httpsResponse = await httpClient.HeadAsync(TestHttpsUri);
@@ -98,5 +97,23 @@ protected override async Task<bool> RunInternalAsync(StringBuilder log, IList<st
 
             return true;
         }
+
+        internal /* For testing purposes */ async void SendHttpRequest(StringBuilder log, HttpClient httpClient)
+        {
+            foreach (var uri in new List<string> { TestHttpUri, TestHttpUriFallback })
+            {
+                try
+                {
+                    log.Append($"Sending HEAD request to {uri}...");
+                    using var httpResponse = await httpClient.HeadAsync(uri);
+                    log.AppendLine(" OK");
+                    break;
+                }
+                catch (HttpRequestException)
+                {
+                    log.AppendLine(" warning: HEAD request failed");
+                }
+            }
+        }
     }
 }
diff --git a/src/shared/TestInfrastructure/Objects/TestHttpMessageHandler.cs b/src/shared/TestInfrastructure/Objects/TestHttpMessageHandler.cs
index 9dce7898f..0a2c46e18 100644
--- a/src/shared/TestInfrastructure/Objects/TestHttpMessageHandler.cs
+++ b/src/shared/TestInfrastructure/Objects/TestHttpMessageHandler.cs
@@ -23,6 +23,8 @@ public class TestHttpMessageHandler : HttpMessageHandler
         public bool ThrowOnUnexpectedRequest { get; set; }
         public bool SimulateNoNetwork { get; set; }
 
+        public bool SimulatePrimaryUriFailure { get; set; }
+
         public IDictionary<(HttpMethod method, Uri uri), int> RequestCounts => _requestCounts;
 
         public void Setup(HttpMethod method, Uri uri, AsyncRequestHandler handler)
@@ -80,6 +82,12 @@ protected override async Task<HttpResponseMessage> SendAsync(HttpRequestMessage
                 throw new HttpRequestException("Simulated no network");
             }
 
+            if (SimulatePrimaryUriFailure && request.RequestUri != null  &&
+                request.RequestUri.ToString().Equals("http://example.com/"))
+            {
+                throw new HttpRequestException("Simulated http failure.");
+            }
+
             foreach (var kvp in _handlers)
             {
                 if (kvp.Key == requestKey)