diff --git a/src/Kestrel.Core/Internal/Infrastructure/KestrelEventSource.cs b/src/Kestrel.Core/Internal/Infrastructure/KestrelEventSource.cs
index ed70a3797a..7faf486d1f 100644
--- a/src/Kestrel.Core/Internal/Infrastructure/KestrelEventSource.cs
+++ b/src/Kestrel.Core/Internal/Infrastructure/KestrelEventSource.cs
@@ -32,8 +32,8 @@ namespace Microsoft.AspNetCore.Server.Kestrel.Core.Internal.Infrastructure
             {
                 ConnectionStart(
                     connection.ConnectionId,
-                    connection.LocalEndPoint.ToString(),
-                    connection.RemoteEndPoint.ToString());
+                    connection.LocalEndPoint?.ToString(),
+                    connection.RemoteEndPoint?.ToString());
             }
         }
 
diff --git a/test/Kestrel.FunctionalTests/AddressRegistrationTests.cs b/test/Kestrel.FunctionalTests/AddressRegistrationTests.cs
index 0c85a2a928..b550c852c7 100644
--- a/test/Kestrel.FunctionalTests/AddressRegistrationTests.cs
+++ b/test/Kestrel.FunctionalTests/AddressRegistrationTests.cs
@@ -40,7 +40,7 @@ namespace Microsoft.AspNetCore.Server.Kestrel.FunctionalTests
         }
 
         [ConditionalFact]
-        [NetworkIsReachable]
+        [HostNameIsReachable]
         public async Task RegisterAddresses_HostName_Success()
         {
             var hostName = Dns.GetHostName();
@@ -308,7 +308,7 @@ namespace Microsoft.AspNetCore.Server.Kestrel.FunctionalTests
         }
 
         [ConditionalFact]
-        [NetworkIsReachable]
+        [HostNameIsReachable]
         public async Task ListenAnyIP_HostName_Success()
         {
             var hostName = Dns.GetHostName();
diff --git a/test/Kestrel.FunctionalTests/TestHelpers/HostNameIsReachableAttribute.cs b/test/Kestrel.FunctionalTests/TestHelpers/HostNameIsReachableAttribute.cs
new file mode 100644
index 0000000000..bd120b6356
--- /dev/null
+++ b/test/Kestrel.FunctionalTests/TestHelpers/HostNameIsReachableAttribute.cs
@@ -0,0 +1,88 @@
+// Copyright (c) .NET Foundation. All rights reserved.
+// Licensed under the Apache License, Version 2.0. See License.txt in the project root for license information.
+
+using System;
+using System.Net;
+using System.Net.Sockets;
+using System.Threading.Tasks;
+using Microsoft.AspNetCore.Testing.xunit;
+
+namespace Microsoft.AspNetCore.Server.Kestrel.FunctionalTests
+{
+    [AttributeUsage(AttributeTargets.Method, AllowMultiple = false)]
+    public class HostNameIsReachableAttribute : Attribute, ITestCondition
+    {
+        private string _hostname;
+        private string _error;
+        private bool? _isMet;
+
+        public bool IsMet
+        {
+            get
+            {
+                return _isMet ?? (_isMet = HostNameIsReachable().GetAwaiter().GetResult()).Value;
+            }
+        }
+
+        public string SkipReason => _hostname != null
+            ? $"Test cannot run when network is unreachable. Socket exception: '{_error}'"
+            : "Could not determine hostname for current test machine";
+
+        private async Task<bool> HostNameIsReachable()
+        {
+            try
+            {
+                _hostname = Dns.GetHostName();
+
+                // if the network is unreachable on macOS, throws with SocketError.NetworkUnreachable
+                // if the network device is not configured, throws with SocketError.HostNotFound
+                // if the network is reachable, throws with SocketError.ConnectionRefused or succeeds
+                var timeoutTask = Task.Delay(1000);
+                if (await Task.WhenAny(ConnectToHost(_hostname, 80), timeoutTask) == timeoutTask)
+                {
+                    _error = "Attempt to establish a connection took over a second without success or failure.";
+                    return false;
+                }
+            }
+            catch (SocketException ex) when (
+                ex.SocketErrorCode == SocketError.NetworkUnreachable
+                || ex.SocketErrorCode == SocketError.HostNotFound)
+            {
+                _error = ex.Message;
+                return false;
+            }
+            catch
+            {
+                // Swallow other errors. Allows the test to throw the failures instead
+            }
+
+            return true;
+        }
+
+        public static async Task<Socket> ConnectToHost(string hostName, int port)
+        {
+            var tcs = new TaskCompletionSource<Socket>();
+
+            var socketArgs = new SocketAsyncEventArgs();
+            socketArgs.RemoteEndPoint = new DnsEndPoint(hostName, port);
+            socketArgs.Completed += (s, e) => tcs.TrySetResult(e.ConnectSocket);
+
+            // Must use static ConnectAsync(), since instance Connect() does not support DNS names on OSX/Linux.
+            if (Socket.ConnectAsync(SocketType.Stream, ProtocolType.Tcp, socketArgs))
+            {
+                await tcs.Task.ConfigureAwait(false);
+            }
+
+            var socket = socketArgs.ConnectSocket;
+
+            if (socket == null)
+            {
+                throw new SocketException((int)socketArgs.SocketError);
+            }
+            else
+            {
+                return socket;
+            }
+        }
+    }
+}
diff --git a/test/Kestrel.FunctionalTests/TestHelpers/NetworkIsReachableAttribute.cs b/test/Kestrel.FunctionalTests/TestHelpers/NetworkIsReachableAttribute.cs
deleted file mode 100644
index 9b62c0689b..0000000000
--- a/test/Kestrel.FunctionalTests/TestHelpers/NetworkIsReachableAttribute.cs
+++ /dev/null
@@ -1,51 +0,0 @@
-// Copyright (c) .NET Foundation. All rights reserved.
-// Licensed under the Apache License, Version 2.0. See License.txt in the project root for license information.
-
-using System;
-using System.Net;
-using System.Net.Sockets;
-using Microsoft.AspNetCore.Testing;
-using Microsoft.AspNetCore.Testing.xunit;
-
-namespace Microsoft.AspNetCore.Server.Kestrel.FunctionalTests
-{
-    [AttributeUsage(AttributeTargets.Method, AllowMultiple = false)]
-    public class NetworkIsReachableAttribute : Attribute, ITestCondition
-    {
-        private string _hostname;
-        private string _error;
-
-        public bool IsMet
-        {
-            get
-            {
-                try
-                {
-                    _hostname = Dns.GetHostName();
-
-                    // if the network is unreachable on macOS, throws with SocketError.NetworkUnreachable
-                    // if the network device is not configured, throws with SocketError.HostNotFound
-                    // if the network is reachable, throws with SocketError.ConnectionRefused or succeeds
-                    HttpClientSlim.GetStringAsync($"http://{_hostname}").GetAwaiter().GetResult();
-                }
-                catch (SocketException ex) when (
-                    ex.SocketErrorCode == SocketError.NetworkUnreachable
-                    || ex.SocketErrorCode == SocketError.HostNotFound)
-                {
-                    _error = ex.Message;
-                    return false;
-                }
-                catch
-                {
-                    // Swallow other errors. Allows the test to throw the failures instead
-                }
-
-                return true;
-            }
-        }
-
-        public string SkipReason => _hostname != null
-            ? $"Test cannot run when network is unreachable. Socket exception: '{_error}'"
-            : "Could not determine hostname for current test machine";
-    }
-}