Now I think that I can use this event and use task scheduler to start the Smart Card service whenever there is this event in the Application Log. I noticed that when I connect using Remote Desktop, the event viewer logs an event “9027” in Application Logs, as shown below.

Now the problem is how can I make sure to start the service when I am connecting via Remote Desktop. I tested it by manually starting the Smart Card service and I was then able to logon to the machine. It looks like when I Remote Desktop from Mac to the Windows machine the Windows machine is unable to detect the Smart Card and therefore the service does not start. The Smart Card service only starts when it detects the Smart Card reader. After doing some research online I found out that Microsoft has changed how Smart Card service behaves in Windows 8 and later. I was expecting that this Smart Card issue would have been resolved in Windows 10 but Windows 10 has the same issue. This was an ok workaround until recently when my Virtual Desktop was upgraded to Windows 10.

The workaround I used for this was to connect to my Windows 7 Virtual Desktop and from there connect to Windows 8, Windows 10 or Windows 2012 R2 machines. When I try to logon to Windows 2012 R2 Server or Windows 8 from Mac using Remote Desktop, I get the error “No valid certificates were found on this smart card” as shown below. It looks like Microsoft has changed the behavior of Smart Card service in Windows 8 and Windows 2012 R2. It stopped working with Windows 8 and Windows 2012 R2. Actually it worked fine until Windows 7 and Windows 2012 Server. I found a nice client Royal TSX that supports Smart Card redirection and it works fine. Even Microsoft Remote Desktop client on Mac currently does not support Smart Card redirection. There aren’t many Remote Desktop client options available for Mac that support Smart Card redirection. The problem occurs when we try to logon to Windows machines from Macs. Even if we use Remote Desktop connection from our Windows desktops to other Windows machines, it works without any issues. It works fine as long as we are logging on to our Macs or our Windows Desktops. At my work we are required to use Smart Card to login to our systems.

Macbook smart card reader