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 9631bb66e8ca5e..3e7f051a18036b 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
@@ -677,8 +677,8 @@ public ValueTask SendFileAsync(string? fileName, ReadOnlyMemory<byte> preBuffer,
 
             if (!IsConnectionOriented)
             {
-                var soex = new SocketException((int)SocketError.NotConnected);
-                return ValueTask.FromException(soex);
+                var ex = new NotSupportedException(SR.net_notconnected);
+                return ValueTask.FromException(ex);
             }
 
             int packetsCount = 0;
diff --git a/src/libraries/System.Net.Sockets/src/System/Net/Sockets/Socket.cs b/src/libraries/System.Net.Sockets/src/System/Net/Sockets/Socket.cs
index 03b6a12b440e73..9c9afb9ffd4241 100644
--- a/src/libraries/System.Net.Sockets/src/System/Net/Sockets/Socket.cs
+++ b/src/libraries/System.Net.Sockets/src/System/Net/Sockets/Socket.cs
@@ -1247,7 +1247,7 @@ public void SendFile(string? fileName, ReadOnlySpan<byte> preBuffer, ReadOnlySpa
         {
             ThrowIfDisposed();
 
-            if (!Connected)
+            if (!IsConnectionOriented || !Connected)
             {
                 throw new NotSupportedException(SR.net_notconnected);
             }
diff --git a/src/libraries/System.Net.Sockets/tests/FunctionalTests/SendFile.cs b/src/libraries/System.Net.Sockets/tests/FunctionalTests/SendFile.cs
index e3d35f285e0630..7a8761397fbf56 100644
--- a/src/libraries/System.Net.Sockets/tests/FunctionalTests/SendFile.cs
+++ b/src/libraries/System.Net.Sockets/tests/FunctionalTests/SendFile.cs
@@ -62,7 +62,6 @@ public async Task FileDoesNotExist_ThrowsFileNotFoundException(bool useOverloadW
         [Theory]
         [InlineData(false)]
         [InlineData(true)]
-        [PlatformSpecific(TestPlatforms.Windows)]
         public async Task UdpConnection_ThrowsException(bool usePreAndPostbufferOverload)
         {
             // Create file to send
@@ -77,16 +76,14 @@ public async Task UdpConnection_ThrowsException(bool usePreAndPostbufferOverload
 
             client.Connect(listener.LocalEndPoint);
 
-            SocketException ex;
             if (usePreAndPostbufferOverload)
             {
-                ex = await Assert.ThrowsAsync<SocketException>(() => SendFileAsync(client, tempFile.Path, Array.Empty<byte>(), Array.Empty<byte>(), TransmitFileOptions.UseDefaultWorkerThread));
+                await Assert.ThrowsAsync<NotSupportedException>(() => SendFileAsync(client, tempFile.Path, Array.Empty<byte>(), Array.Empty<byte>(), TransmitFileOptions.UseDefaultWorkerThread));
             }
             else
             {
-                ex = await Assert.ThrowsAsync<SocketException>(() => SendFileAsync(client, tempFile.Path));
+                await Assert.ThrowsAsync<NotSupportedException>(() => SendFileAsync(client, tempFile.Path));
             }
-            Assert.Equal(SocketError.NotConnected, ex.SocketErrorCode);
         }
 
         public static IEnumerable<object[]> SendFile_MemberData()