diff --git a/Snowflake.Data.Tests/IntegrationTests/SFConnectionIT.cs b/Snowflake.Data.Tests/IntegrationTests/SFConnectionIT.cs
index fdcd0508b..ddd73167d 100644
--- a/Snowflake.Data.Tests/IntegrationTests/SFConnectionIT.cs
+++ b/Snowflake.Data.Tests/IntegrationTests/SFConnectionIT.cs
@@ -3,6 +3,7 @@
  */
 
 using System.Data.Common;
+using System.Net;
 using Snowflake.Data.Tests.Util;
 
 namespace Snowflake.Data.Tests.IntegrationTests
@@ -520,12 +521,12 @@ public void TestDefaultLoginTimeout()
         }
 
         [Test]
-        public void TestConnectionFailFast()
+        public void TestConnectionFailFastForNonRetried404OnLogin()
         {
             using (var conn = new SnowflakeDbConnection())
             {
                 // Just a way to get a 404 on the login request and make sure there are no retry
-                string invalidConnectionString = "host=learn.microsoft.com;"
+                string invalidConnectionString = "host=google.com/404;"
                     + "connection_timeout=0;account=testFailFast;user=testFailFast;password=testFailFast;";
 
                 conn.ConnectionString = invalidConnectionString;
@@ -538,8 +539,12 @@ public void TestConnectionFailFast()
                 }
                 catch (SnowflakeDbException e)
                 {
-                    Assert.AreEqual(SFError.INTERNAL_ERROR.GetAttribute<SFErrorAttr>().errorCode,
-                        e.ErrorCode);
+                    SnowflakeDbExceptionAssert.HasHttpErrorCodeInExceptionChain(e, HttpStatusCode.NotFound);
+                    SnowflakeDbExceptionAssert.HasMessageInExceptionChain(e, "404 (Not Found)");
+                }
+                catch (Exception unexpected)
+                {
+                    Assert.Fail($"Unexpected {unexpected.GetType()} exception occurred");
                 }
 
                 Assert.AreEqual(ConnectionState.Closed, conn.State);
@@ -547,11 +552,11 @@ public void TestConnectionFailFast()
         }
 
         [Test]
-        public void TestEnableRetry()
+        public void TestEnableLoginRetryOn404()
         {
             using (var conn = new SnowflakeDbConnection())
             {
-                string invalidConnectionString = "host=learn.microsoft.com;"
+                string invalidConnectionString = "host=google.com/404;"
                     + "connection_timeout=0;account=testFailFast;user=testFailFast;password=testFailFast;disableretry=true;forceretryon404=true";
                 conn.ConnectionString = invalidConnectionString;
 
@@ -563,8 +568,12 @@ public void TestEnableRetry()
                 }
                 catch (SnowflakeDbException e)
                 {
-                    Assert.AreEqual(SFError.INTERNAL_ERROR.GetAttribute<SFErrorAttr>().errorCode,
-                        e.ErrorCode);
+                    SnowflakeDbExceptionAssert.HasErrorCode(e, SFError.INTERNAL_ERROR);
+                    SnowflakeDbExceptionAssert.HasHttpErrorCodeInExceptionChain(e, HttpStatusCode.NotFound);
+                }
+                catch (Exception unexpected)
+                {
+                    Assert.Fail($"Unexpected {unexpected.GetType()} exception occurred");
                 }
 
                 Assert.AreEqual(ConnectionState.Closed, conn.State);
@@ -1947,12 +1956,12 @@ public void TestAsyncDefaultLoginTimeout()
         }
 
         [Test]
-        public void TestAsyncConnectionFailFast()
+        public void TestAsyncConnectionFailFastForNonRetried404OnLogin()
         {
             using (var conn = new SnowflakeDbConnection())
             {
                 // Just a way to get a 404 on the login request and make sure there are no retry
-                string invalidConnectionString = "host=learn.microsoft.com;"
+                string invalidConnectionString = "host=google.com/404;"
                     + "connection_timeout=0;account=testFailFast;user=testFailFast;password=testFailFast;";
 
                 conn.ConnectionString = invalidConnectionString;
@@ -1967,7 +1976,12 @@ public void TestAsyncConnectionFailFast()
                 }
                 catch (AggregateException e)
                 {
-                    SnowflakeDbExceptionAssert.HasErrorCode((SnowflakeDbException)e.InnerException, SFError.INTERNAL_ERROR);
+                    SnowflakeDbExceptionAssert.HasHttpErrorCodeInExceptionChain(e, HttpStatusCode.NotFound);
+                    SnowflakeDbExceptionAssert.HasMessageInExceptionChain(e, "404 (Not Found)");
+                }
+                catch (Exception unexpected)
+                {
+                    Assert.Fail($"Unexpected {unexpected.GetType()} exception occurred");
                 }
 
                 Assert.AreEqual(ConnectionState.Closed, conn.State);
diff --git a/Snowflake.Data.Tests/Util/SnowflakeDbExceptionAssert.cs b/Snowflake.Data.Tests/Util/SnowflakeDbExceptionAssert.cs
index b3d3e50db..a1a166f86 100644
--- a/Snowflake.Data.Tests/Util/SnowflakeDbExceptionAssert.cs
+++ b/Snowflake.Data.Tests/Util/SnowflakeDbExceptionAssert.cs
@@ -1,3 +1,8 @@
+using System;
+using System.Collections.Generic;
+using System.Linq;
+using System.Net;
+using System.Net.Http;
 using Snowflake.Data.Core;
 using Snowflake.Data.Client;
 using NUnit.Framework;
@@ -10,5 +15,69 @@ public static void HasErrorCode(SnowflakeDbException exception, SFError sfError)
         {
             Assert.AreEqual(exception.ErrorCode, sfError.GetAttribute<SFErrorAttr>().errorCode);
         }
+        
+        public static void HasErrorCode(Exception exception, SFError sfError)
+        {
+            Assert.NotNull(exception);
+            switch (exception)
+            {
+                case SnowflakeDbException snowflakeDbException:
+                    Assert.AreEqual(snowflakeDbException.ErrorCode, sfError.GetAttribute<SFErrorAttr>().errorCode);
+                    break;
+                default:
+                    Assert.Fail(exception.GetType() + " type is not " + typeof(SnowflakeDbException));
+                    break;
+            }
+        }
+
+        public static void HasHttpErrorCodeInExceptionChain(Exception exception, HttpStatusCode expected)
+        {
+            var exceptions = CollectExceptions(exception);
+            Assert.AreEqual(true,
+                exceptions.Any(e =>
+                {
+                    switch (e)
+                    {
+                        case SnowflakeDbException se:
+                            return se.ErrorCode == (int)expected;
+                        case HttpRequestException he:
+                            return he.StatusCode == expected;
+                        default:
+                            return false;
+                    }
+                }),
+                $"Any of exceptions in the chain should have HTTP Status: {expected}");
+        }
+
+        public static void HasMessageInExceptionChain(Exception exception, string expected)
+        {
+            var exceptions = CollectExceptions(exception);
+            Assert.AreEqual(true,
+                exceptions.Any(e => e.Message.Contains(expected)),
+                $"Any of exceptions in the chain should contain message: {expected}");
+        }
+
+        private static List<Exception> CollectExceptions(Exception exception)
+        {
+            var collected = new List<Exception>();
+            if (exception is null)
+                return collected;
+            switch (exception)
+            {
+                case AggregateException aggregate:
+                    var inner = aggregate.Flatten().InnerExceptions;
+                    // collected.AddRange(inner.OfType<SnowflakeDbException>());
+                    collected.AddRange(inner);
+                    collected.AddRange(inner
+                        .Where(e => e.InnerException != null)
+                        .SelectMany(e => CollectExceptions(e.InnerException)));
+                    break;
+                case Exception general:
+                    collected.AddRange(CollectExceptions(general.InnerException));
+                    collected.Add(general);
+                    break;
+            }
+            return collected;
+        }
     }
 }