For any issue, it's useful to have the user run the License Health Check tool (Bentley.Licensing.HealthCheck.exe) located here:
C:\Program Files\Common Files\Bentley Shared\CONNECTION Client\LicService\
C:\Program Files\Common Files\Bentley Shared\CONNECTION Client\LicenseService\
Executing Run Check will run through some standard connectivity tests to ensure everything is up and running and accessible from that machine.
Select Tab, press Run Check button, program will perform test and show results.
See Also
Subscription Entitlement Service Failed
Subscription Entitlement Serviceg