I’m using a Let’s Encrypt SSL certificate with Remote Desktop Services and have set up a script to automatically renew the certificate and also update the certificate for the Remote Desktop Services.
The script renews the certificate just fine but after the has been rebooted I can no longer connect via RDP and I get the error ‘An internal error has occured’. Not very informative. The server is a Azure VM and I tried every suggestion I could find including restarting, redeploying and resetting the password. The boot diagnostics wouldn’t even update the screenshot.
I bet there are more ways to solve this, but here’s what works for me.
On another server in the same domain, start the Server Manager. Click on ‘Add other servers to manage’ and select the troubled server and add it. Wait while the servers roles are being fetched. The ‘Remote Desktop Services’ role should appear on the list to the left. Click on it and on the ‘DEPLOYMENT OVERVIEW’ under ‘TASKS’ select ‘Edit Deployment Properties’.
Now select Certificates, select ‘RD Connection Broker – Enable Single Sign On’ and click the ‘Select existing certificate…’ button.
Enter the password for the certificate (or choose a different certificate) and mark ‘Allow the certificate to be added to the Trusted Root…’. Click OK.
That’s what I had to do to fix my problem, hope this will save someone else some time. Now I just have to figure out what I have to do to prevent it from happening every time the certificate is renewed.