diff --git a/src/client/Microsoft.Identity.Client/Http/HttpManager.cs b/src/client/Microsoft.Identity.Client/Http/HttpManager.cs
index f2a0991098..9fd0b66851 100644
--- a/src/client/Microsoft.Identity.Client/Http/HttpManager.cs
+++ b/src/client/Microsoft.Identity.Client/Http/HttpManager.cs
@@ -136,9 +136,10 @@ public async Task<HttpResponse> SendRequestAsync(
             // package 500 errors in a "service not available" exception
             if ((int)response.StatusCode >= 500 && (int)response.StatusCode < 600)
             {
+                string requestUriScrubbed = $"{endpoint.AbsoluteUri.Split('?')[0]}";
                 throw MsalServiceExceptionFactory.FromHttpResponse(
                     MsalError.ServiceNotAvailable,
-                    "Service is unavailable to process the request",
+                    $"Service is unavailable to process the request. The request Uri is: {requestUriScrubbed} on port {endpoint.Port}",
                     response);
             }
 
diff --git a/tests/Microsoft.Identity.Test.Unit/PublicApiTests/ConfidentialClientApplicationTests.cs b/tests/Microsoft.Identity.Test.Unit/PublicApiTests/ConfidentialClientApplicationTests.cs
index a7164ec13f..e9212e5446 100644
--- a/tests/Microsoft.Identity.Test.Unit/PublicApiTests/ConfidentialClientApplicationTests.cs
+++ b/tests/Microsoft.Identity.Test.Unit/PublicApiTests/ConfidentialClientApplicationTests.cs
@@ -23,6 +23,7 @@
 using Microsoft.VisualStudio.TestTools.UnitTesting;
 using NSubstitute;
 using Microsoft.Identity.Client.Extensibility;
+using System.Net;
 
 namespace Microsoft.Identity.Test.Unit.PublicApiTests
 {
@@ -423,6 +424,61 @@ public async Task ConfidentialClientUsingAdfsAsync()
             }
         }
 
+        [TestMethod]
+        public async Task ClientCreds_And_AAD_LogRequestUri_OnServerError_Async()
+        {
+            using (var httpManager = new MockHttpManager())
+            {
+                var cca = ConfidentialClientApplicationBuilder.Create(TestConstants.ClientId)
+                                                              .WithAuthority(new Uri(ClientApplicationBase.DefaultAuthority), true)
+                                                              .WithClientSecret(TestConstants.ClientSecret)
+                                                              .WithHttpManager(httpManager)
+                                                              .WithExtraQueryParameters("parameter=x")
+                                                              .BuildConcrete();
+                var appCacheAccess = cca.AppTokenCache.RecordAccess();
+                var userCacheAccess = cca.UserTokenCache.RecordAccess();
+
+                httpManager.AddInstanceDiscoveryMockHandler();
+                httpManager.AddResiliencyMessageMockHandler(HttpMethod.Post, HttpStatusCode.InternalServerError, retryAfter: 0);
+
+                // Acquire Token
+                var ex = await AssertException.TaskThrowsAsync<MsalServiceException>(
+                    () => cca.AcquireTokenForClient(TestConstants.s_scope.ToArray()).ExecuteAsync())
+                    .ConfigureAwait(false);
+
+                //Assert
+                Assert.AreEqual(MsalError.ServiceNotAvailable, ex.ErrorCode);
+                Assert.IsTrue(ex.Message.Contains(ClientApplicationBase.DefaultAuthority + "oauth2/v2.0/token"));
+            }
+        }
+
+        [TestMethod]
+        public async Task ClientCreds_And_ADFS_LogRequestUri_OnServerError_Async()
+        {
+            using (var httpManager = new MockHttpManager())
+            {
+                var cca = ConfidentialClientApplicationBuilder.Create(TestConstants.ClientId)
+                                                              .WithAuthority(new Uri(TestConstants.OnPremiseAuthority), false)
+                                                              .WithClientSecret(TestConstants.ClientSecret)
+                                                              .WithHttpManager(httpManager)
+                                                              .WithExtraQueryParameters("parameter=x")
+                                                              .BuildConcrete();
+                var appCacheAccess = cca.AppTokenCache.RecordAccess();
+                var userCacheAccess = cca.UserTokenCache.RecordAccess();
+
+                httpManager.AddResiliencyMessageMockHandler(HttpMethod.Post, HttpStatusCode.InternalServerError, retryAfter: 0);
+
+                // Acquire Token
+                var ex = await AssertException.TaskThrowsAsync<MsalServiceException>(
+                    () => cca.AcquireTokenForClient(TestConstants.s_scope.ToArray()).ExecuteAsync())
+                    .ConfigureAwait(false);
+
+                //Assert
+                Assert.AreEqual(MsalError.ServiceNotAvailable, ex.ErrorCode);
+                Assert.IsTrue(ex.Message.Contains(TestConstants.OnPremiseAuthority + "oauth2/token"));
+            }
+        }
+
         private enum CredentialType
         {
             Certificate,