Additional trouble shooting tips for this issue resulting from cases that I have come across.
This Wiki item No Entitlement only covers two cases where this occurs. However it may be a symptom of connection problems with the Subscription Entitlement service. So if you are signed in and you know that you have a valid license/entitlement then try the following steps.
If not all the tests are successful (Green), then review the results window for additional information to help with identifying the issue. This information can be passed on to your IT service desk and/or Bentley support for further assistance.
Ensure that you have the latest version of the Connection Client installed. Occasionally the automatic/ software updates service fails to install this and you have to download and install it manually. This recently helped resolve certificate issues where the certificate for the server was not trusted due to it having expired.