Hi,
R. Cord here, Independent Expert. Hope you are doing well.
Let me suggest some first tips:
If your certificate is for a machine named "server.domain.com" and you access it by IP or simply by "server," you'll get the first error. Change your RDP connection to connect to the full FQDN and the first message should also go away.
Recommendation:
If problem happens after system upgrade to Windows 10 version 1803, please make sure that you also had KB4103721 installed on your Windows 10 1803:
https://support.microsoft.com/en-us/help/4103721
other fix:
Check if the server name in the Remote Desktop Connection settings is different from the name on the certificate, which is causing the error message to appear. To resolve this issue, try next steps:
Open the Remote Desktop Connection application on your computer.
Click on the "Show Options" button.
Click on the "Advanced" tab.
Under the "Server Authentication" section, select "Warn me if the remote computer does not support SSL" and "Do not connect if authentication fails".
Close the options window and try to connect again.
If the above steps do not resolve the issue, you can try the following:
Check that the computer name or IP address you are trying to connect to is correct.
Verify that the Remote Desktop Services is running on the remote computer.
Check that the firewall is not blocking the Remote Desktop Connection.
Verify that the date and time settings on both the local and remote computers are correct.
Try connecting to the remote computer using a different username or password.
Try creating a new Remote Desktop Connection shortcut with the correct settings.
Please let me know if you would like further assistance.
With best Regards,
R. Cord