diff --git a/src/libraries/System.Net.Sockets/src/System/Net/Sockets/MultipleConnectAsync.cs b/src/libraries/System.Net.Sockets/src/System/Net/Sockets/MultipleConnectAsync.cs
index c201d247f9edf3..816a6cab8c70f8 100644
--- a/src/libraries/System.Net.Sockets/src/System/Net/Sockets/MultipleConnectAsync.cs
+++ b/src/libraries/System.Net.Sockets/src/System/Net/Sockets/MultipleConnectAsync.cs
@@ -239,7 +239,10 @@ private void InternalConnectCallback(object? sender, SocketAsyncEventArgs args)
 
                 SocketAsyncEventArgs args = _internalArgs!;
                 args.RemoteEndPoint = new IPEndPoint(attemptAddress, _endPoint!.Port);
-                if (!attemptSocket.ConnectAsync(args))
+                bool pending = attemptSocket.ConnectAsync(args);
+                // Copy the socket address so we can use it in exception message.
+                _userArgs!._socketAddress = _internalArgs!._socketAddress;
+                if (!pending)
                 {
                     InternalConnectCallback(null, args);
                 }
diff --git a/src/libraries/System.Net.Sockets/src/System/Net/Sockets/Socket.Tasks.cs b/src/libraries/System.Net.Sockets/src/System/Net/Sockets/Socket.Tasks.cs
index cde90ae0931cc5..9fc5fbf961f4b8 100644
--- a/src/libraries/System.Net.Sockets/src/System/Net/Sockets/Socket.Tasks.cs
+++ b/src/libraries/System.Net.Sockets/src/System/Net/Sockets/Socket.Tasks.cs
@@ -6,6 +6,7 @@
 using System.Collections.Generic;
 using System.Diagnostics;
 using System.IO;
+using System.Net.Internals;
 using System.Runtime.CompilerServices;
 using System.Runtime.ExceptionServices;
 using System.Runtime.InteropServices;
@@ -1140,7 +1141,10 @@ private void ThrowException(SocketError error, CancellationToken cancellationTok
 
             private Exception CreateException(SocketError error, bool forAsyncThrow = true)
             {
-                Exception e = new SocketException((int)error);
+                // When available, include the IP endpoint information in connection exceptions:
+                Exception e = LastOperation == SocketAsyncOperation.Connect && _socketAddress != null ?
+                    SocketExceptionFactory.CreateSocketException((int)error, _socketAddress.GetIPEndPoint()) :
+                    new SocketException((int)error);
 
                 if (forAsyncThrow)
                 {
diff --git a/src/libraries/System.Net.Sockets/tests/FunctionalTests/Connect.cs b/src/libraries/System.Net.Sockets/tests/FunctionalTests/Connect.cs
index d4bdcfed80a0f6..e8b8cd665b0348 100644
--- a/src/libraries/System.Net.Sockets/tests/FunctionalTests/Connect.cs
+++ b/src/libraries/System.Net.Sockets/tests/FunctionalTests/Connect.cs
@@ -82,6 +82,20 @@ public async Task Connect_MultipleIPAddresses_Success(IPAddress listenAt)
             }
         }
 
+        [OuterLoop("Slow on Windows")]
+        [Theory]
+        [InlineData(false)]
+        [InlineData(true)]
+        public virtual async Task Connect_WhenFails_ThrowsSocketExceptionWithIPEndpointInfo(bool useDns)
+        {
+            // Port 288 is unassigned:
+            // https://www.iana.org/assignments/service-names-port-numbers/service-names-port-numbers.txt
+            EndPoint badEndpoint = useDns ? (EndPoint)new DnsEndPoint("localhost", 288) : new IPEndPoint(IPAddress.Loopback, 288);
+            using Socket client = new Socket(AddressFamily.InterNetwork, SocketType.Stream, ProtocolType.Tcp);
+            SocketException ex = await Assert.ThrowsAnyAsync<SocketException>(() => ConnectAsync(client, badEndpoint));
+            Assert.Contains("127.0.0.1:288", ex.Message);
+        }
+
         [Fact]
         public async Task Connect_OnConnectedSocket_Fails()
         {
@@ -115,7 +129,7 @@ public async Task Connect_AfterDisconnect_Fails()
                 }
                 else
                 {
-                    SocketException se = await Assert.ThrowsAsync<SocketException>(() => ConnectAsync(client, new IPEndPoint(IPAddress.Loopback, port)));
+                    SocketException se = await Assert.ThrowsAnyAsync<SocketException>(() => ConnectAsync(client, new IPEndPoint(IPAddress.Loopback, port)));
                     Assert.Equal(SocketError.IsConnected, se.SocketErrorCode);
                 }
             }
@@ -204,5 +218,8 @@ public ConnectTask(ITestOutputHelper output) : base(output) {}
     public sealed class ConnectEap : Connect<SocketHelperEap>
     {
         public ConnectEap(ITestOutputHelper output) : base(output) {}
+
+        // We should skip this since the exception creation logic is defined in SocketHelperEap.
+        public override Task Connect_WhenFails_ThrowsSocketExceptionWithIPEndpointInfo(bool useDns) => Task.CompletedTask;
     }
 }