diff --git a/src/Microsoft.AspNetCore.Server.Kestrel/KestrelServer.cs b/src/Microsoft.AspNetCore.Server.Kestrel/KestrelServer.cs
index 0bf4baf9c9..d9844714de 100644
--- a/src/Microsoft.AspNetCore.Server.Kestrel/KestrelServer.cs
+++ b/src/Microsoft.AspNetCore.Server.Kestrel/KestrelServer.cs
@@ -3,6 +3,7 @@
 
 using System;
 using System.Collections.Generic;
+using System.IO;
 using System.Linq;
 using System.Reflection;
 using Microsoft.AspNetCore.Hosting;
@@ -109,8 +110,19 @@ namespace Microsoft.AspNetCore.Server.Kestrel
 
                     if (!parsedAddress.Host.Equals("localhost", StringComparison.OrdinalIgnoreCase))
                     {
-                        _disposables.Push(engine.CreateServer(
-                            parsedAddress));
+                        try
+                        {
+                            _disposables.Push(engine.CreateServer(parsedAddress));
+                        }
+                        catch (AggregateException ex)
+                        {
+                            if ((ex.InnerException as UvException)?.StatusCode == Constants.EADDRINUSE)
+                            {
+                                throw new IOException($"Failed to bind to address {parsedAddress}: address already in use.", ex);
+                            }
+
+                            throw;
+                        }
                     }
                     else
                     {
@@ -120,24 +132,22 @@ namespace Microsoft.AspNetCore.Server.Kestrel
                         }
 
                         var ipv4Address = parsedAddress.WithHost("127.0.0.1");
-                        var exceptions = new List<UvException>();
+                        var exceptions = new List<Exception>();
 
                         try
                         {
                             _disposables.Push(engine.CreateServer(ipv4Address));
                         }
-                        catch (AggregateException ex)
+                        catch (AggregateException ex) when (ex.InnerException is UvException)
                         {
-                            var uvException = ex.InnerException as UvException;
-
-                            if (uvException != null && uvException.StatusCode != Constants.EADDRINUSE)
+                            if ((ex.InnerException as UvException).StatusCode == Constants.EADDRINUSE)
                             {
-                                _logger.LogWarning(0, ex, $"Unable to bind to {parsedAddress.ToString()} on the IPv4 loopback interface.");
-                                exceptions.Add(uvException);
+                                throw new IOException($"Failed to bind to address {parsedAddress.ToString()} on the IPv4 loopback interface: port already in use.", ex);
                             }
                             else
                             {
-                                throw;
+                                _logger.LogWarning(0, ex, $"Unable to bind to {parsedAddress.ToString()} on the IPv4 loopback interface.");
+                                exceptions.Add(ex.InnerException);
                             }
                         }
 
@@ -147,26 +157,22 @@ namespace Microsoft.AspNetCore.Server.Kestrel
                         {
                             _disposables.Push(engine.CreateServer(ipv6Address));
                         }
-                        catch (AggregateException ex)
+                        catch (AggregateException ex) when (ex.InnerException is UvException)
                         {
-                            var uvException = ex.InnerException as UvException;
-
-                            if (uvException != null && uvException.StatusCode != Constants.EADDRINUSE)
+                            if ((ex.InnerException as UvException).StatusCode == Constants.EADDRINUSE)
                             {
-                                _logger.LogWarning(0, ex, $"Unable to bind to {parsedAddress.ToString()} on the IPv6 loopback interface.");
-                                exceptions.Add(uvException);
+                                throw new IOException($"Failed to bind to address {parsedAddress.ToString()} on the IPv6 loopback interface: port already in use.", ex);
                             }
                             else
                             {
-                                throw;
+                                _logger.LogWarning(0, ex, $"Unable to bind to {parsedAddress.ToString()} on the IPv6 loopback interface.");
+                                exceptions.Add(ex.InnerException);
                             }
                         }
 
                         if (exceptions.Count == 2)
                         {
-                            var ex = new AggregateException(exceptions);
-                            _logger.LogError(0, ex, $"Unable to bind to {parsedAddress.ToString()} on any loopback interface.");
-                            throw ex;
+                            throw new IOException($"Failed to bind to address {parsedAddress.ToString()}.", new AggregateException(exceptions));
                         }
                     }
 
diff --git a/test/Microsoft.AspNetCore.Server.Kestrel.FunctionalTests/AddressRegistrationTests.cs b/test/Microsoft.AspNetCore.Server.Kestrel.FunctionalTests/AddressRegistrationTests.cs
index a438309246..be37bf0674 100644
--- a/test/Microsoft.AspNetCore.Server.Kestrel.FunctionalTests/AddressRegistrationTests.cs
+++ b/test/Microsoft.AspNetCore.Server.Kestrel.FunctionalTests/AddressRegistrationTests.cs
@@ -3,6 +3,7 @@
 
 using System;
 using System.Collections.Generic;
+using System.IO;
 using System.Linq;
 using System.Net;
 using System.Net.NetworkInformation;
@@ -97,6 +98,49 @@ namespace Microsoft.AspNetCore.Server.Kestrel.FunctionalTests
             }
         }
 
+        [Fact]
+        public void ThrowsWhenBindingToIPv4AddressInUse()
+        {
+            using (var socket = new Socket(AddressFamily.InterNetwork, SocketType.Stream, ProtocolType.Tcp))
+            {
+                var port = GetNextPort();
+                socket.Bind(new IPEndPoint(IPAddress.Loopback, port));
+
+                var hostBuilder = new WebHostBuilder()
+                    .UseKestrel()
+                    .UseUrls($"http://127.0.0.1:{port}")
+                    .Configure(ConfigureEchoAddress);
+
+                using (var host = hostBuilder.Build())
+                {
+                    var exception = Assert.Throws<IOException>(() => host.Start());
+                    Assert.Equal($"Failed to bind to address http://127.0.0.1:{port}: address already in use.", exception.Message);
+                }
+            }
+        }
+
+        [ConditionalFact]
+        [IPv6SupportedCondition]
+        public void ThrowsWhenBindingToIPv6AddressInUse()
+        {
+            using (var socket = new Socket(AddressFamily.InterNetworkV6, SocketType.Stream, ProtocolType.Tcp))
+            {
+                var port = GetNextPort();
+                socket.Bind(new IPEndPoint(IPAddress.IPv6Loopback, port));
+
+                var hostBuilder = new WebHostBuilder()
+                    .UseKestrel()
+                    .UseUrls($"http://[::1]:{port}")
+                    .Configure(ConfigureEchoAddress);
+
+                using (var host = hostBuilder.Build())
+                {
+                    var exception = Assert.Throws<IOException>(() => host.Start());
+                    Assert.Equal($"Failed to bind to address http://[::1]:{port}: address already in use.", exception.Message);
+                }
+            }
+        }
+
         [Fact]
         public void ThrowsWhenBindingLocalhostToIPv4AddressInUse()
         {
@@ -138,8 +182,10 @@ namespace Microsoft.AspNetCore.Server.Kestrel.FunctionalTests
 
                 using (var host = hostBuilder.Build())
                 {
-                    var exception = Assert.Throws<AggregateException>(() => host.Start());
-                    Assert.Contains(exception.InnerExceptions, ex => ex is UvException);
+                    var exception = Assert.Throws<IOException>(() => host.Start());
+                    Assert.Equal(
+                        $"Failed to bind to address http://localhost:{port} on the {(addressFamily == AddressFamily.InterNetwork ? "IPv4" : "IPv6")} loopback interface: port already in use.",
+                        exception.Message);
                 }
             }
         }