diff --git a/src/Servers/Kestrel/Core/test/TlsListenerTests.cs b/src/Servers/Kestrel/Core/test/TlsListenerTests.cs
index 4bce89de208d..6350465dbe41 100644
--- a/src/Servers/Kestrel/Core/test/TlsListenerTests.cs
+++ b/src/Servers/Kestrel/Core/test/TlsListenerTests.cs
@@ -70,9 +70,7 @@ public async Task RunTlsClientHelloCallbackTest_WithExtraShortLastingToken()
         var cts = new CancellationTokenSource(TimeSpan.FromMilliseconds(3));
 
         await writer.WriteAsync(new byte[1] { 0x16 });
-        await VerifyThrowsAnyAsync(
-            async () => await listener.OnTlsClientHelloAsync(transportConnection, cts.Token),
-            typeof(OperationCanceledException), typeof(TaskCanceledException));
+        await Assert.ThrowsAnyAsync<OperationCanceledException>(() => listener.OnTlsClientHelloAsync(transportConnection, cts.Token));
         Assert.False(tlsClientHelloCallbackInvoked);
     }
 
@@ -95,9 +93,7 @@ public async Task RunTlsClientHelloCallbackTest_WithPreCanceledToken()
         cts.Cancel();
 
         await writer.WriteAsync(new byte[1] { 0x16 });
-        await VerifyThrowsAnyAsync(
-            async () => await listener.OnTlsClientHelloAsync(transportConnection, cts.Token),
-            typeof(OperationCanceledException), typeof(TaskCanceledException));
+        await Assert.ThrowsAnyAsync<OperationCanceledException>(() => listener.OnTlsClientHelloAsync(transportConnection, cts.Token));
         Assert.False(tlsClientHelloCallbackInvoked);
     }
 
@@ -122,7 +118,7 @@ public async Task RunTlsClientHelloCallbackTest_WithPendingCancellation()
         await writer.WriteAsync(new byte[2] { 0x03, 0x01 });
         cts.Cancel();
 
-        await Assert.ThrowsAsync<OperationCanceledException>(async () => await listenerTask);
+        await Assert.ThrowsAnyAsync<OperationCanceledException>(() => listenerTask);
         Assert.False(tlsClientHelloCallbackInvoked);
     }
 
@@ -158,8 +154,8 @@ public async Task RunTlsClientHelloCallbackTest_DeterministicallyReads()
         Assert.Equal(5, readResult.Buffer.Length);
 
         // ensuring that we have read limited number of times
-        Assert.True(reader.ReadAsyncCounter is >= 2 && reader.ReadAsyncCounter is <= 4,
-            $"Expected ReadAsync() to happen about 2-4 times. Actually happened {reader.ReadAsyncCounter} times.");
+        Assert.True(reader.ReadAsyncCounter is >= 2 && reader.ReadAsyncCounter is <= 5,
+            $"Expected ReadAsync() to happen about 2-5 times. Actually happened {reader.ReadAsyncCounter} times.");
     }
 
     private async Task RunTlsClientHelloCallbackTest_WithMultipleSegments(
@@ -623,28 +619,4 @@ public static IEnumerable<object[]> InvalidClientHelloData_Segmented()
         _invalidTlsClientHelloHeader, _invalid3BytesMessage, _invalid9BytesMessage,
         _invalidUnknownProtocolVersion1, _invalidUnknownProtocolVersion2, _invalidIncorrectHandshakeMessageType
     };
-
-    static async Task VerifyThrowsAnyAsync(Func<Task> code, params Type[] exceptionTypes)
-    {
-        if (exceptionTypes == null || exceptionTypes.Length == 0)
-        {
-            throw new ArgumentException("At least one exception type must be provided.", nameof(exceptionTypes));
-        }
-
-        try
-        {
-            await code();
-        }
-        catch (Exception ex)
-        {
-            if (exceptionTypes.Any(type => type.IsInstanceOfType(ex)))
-            {
-                return;
-            }
-
-            throw ThrowsException.ForIncorrectExceptionType(exceptionTypes.First(), ex);
-        }
-
-        throw ThrowsException.ForNoException(exceptionTypes.First());
-    }
 }
diff --git a/src/Servers/Kestrel/test/InMemory.FunctionalTests/TlsListenerTests.cs b/src/Servers/Kestrel/test/InMemory.FunctionalTests/TlsListenerTests.cs
index f91ea27eae8f..f835e452ff21 100644
--- a/src/Servers/Kestrel/test/InMemory.FunctionalTests/TlsListenerTests.cs
+++ b/src/Servers/Kestrel/test/InMemory.FunctionalTests/TlsListenerTests.cs
@@ -3,6 +3,7 @@
 
 using System;
 using System.Collections.Generic;
+using System.IO.Pipelines;
 using System.Net;
 using System.Net.Security;
 using System.Security.Authentication;
@@ -18,6 +19,8 @@
 using Microsoft.Extensions.DependencyInjection;
 using Microsoft.Extensions.Hosting;
 using Microsoft.Extensions.Logging;
+using Newtonsoft.Json.Linq;
+using Xunit.Sdk;
 
 namespace InMemory.FunctionalTests;
 
@@ -66,4 +69,40 @@ await sslStream.AuthenticateAsClientAsync(new SslClientAuthenticationOptions
 
         Assert.True(tlsClientHelloCallbackInvoked);
     }
+
+    [Fact]
+    public async Task TlsClientHelloBytesCallback_UsesOptionsTimeout()
+    {
+        var tlsClientHelloCallbackInvoked = false;
+        var testContext = new TestServiceContext(LoggerFactory);
+        await using (var server = new TestServer(context => Task.CompletedTask,
+            testContext,
+            listenOptions =>
+            {
+                listenOptions.UseHttps(_x509Certificate2, httpsOptions =>
+                {
+                    httpsOptions.HandshakeTimeout = TimeSpan.FromMilliseconds(1);
+
+                    httpsOptions.TlsClientHelloBytesCallback = (connection, clientHelloBytes) =>
+                    {
+                        Logger.LogDebug("[Received TlsClientHelloBytesCallback] Connection: {0}; TLS client hello buffer: {1}", connection.ConnectionId, clientHelloBytes.Length);
+                        tlsClientHelloCallbackInvoked = true;
+                        Assert.True(clientHelloBytes.Length > 32);
+                        Assert.NotNull(connection);
+                    };
+                });
+            }))
+        {
+            using (var connection = server.CreateConnection())
+            {
+                await connection.TransportConnection.Input.WriteAsync(new byte[] { 0x16 });
+                var readResult = await connection.TransportConnection.Output.ReadAsync();
+
+                // HttpsConnectionMiddleware catches the exception, so we can only check the effects of the timeout here
+                Assert.True(readResult.IsCompleted);
+            }
+        }
+
+        Assert.False(tlsClientHelloCallbackInvoked);
+    }
 }