This is something I encountered at a client and I figured that I should write it here because it took a while to find the solution and the only answer came via a support ticket to MS.
A while back when Azure DevOps was called VSTS or Visual Studio Online, you had the possibility to link the tenant to your Azure subscription for billing purposes. This thing allowed you to purchase basic use right licenses to the platform and it even allowed you to purchase Visual Studio Professional licenses which allowed you to license the user VS Pro installations via the platform.
The problem that I faced with this customer was that he was in this position and suddenly they started facing issues with the VS Pro licenses starting to expire and not working anymore. We tried figuring out what was the problem and why it didn’t work but unfortunately we hit a dead end and had to open a support ticket so we can get some assistance while in parallel we were investigating.
We knew that Visual Studio monthly licenses were located in the marketplace –https://marketplace.visualstudio.com/items?itemName=ms.vs-professional-monthly – but we didn’t understand the correlation between one and another.
On a hunch we purchased a few VS Pro Monthly licenses for some users to test out a theory and the lucky part was it worked but we didn’t have an answer as to why the issue existed.
The answer came from the support person on MS end which provided an awesome explanation as to why the problem existed and how to basically fix it.
The problem was that licensing users via the Azure Portal was deprecated a while ago and MS didn’t have a solution for seamless migrations to the new licensing model, so they allowed it to work for existing customers while they removed the capability from the portal.
The licenses that appeared on the billing invoice were called “VSPRO – Monthly” which coincidentally matches the name with the VS Pro licenses from the marketplace. The reality was that the licenses that you could get from the Azure Portal were “Professional” Licenses which were tied to the old VSOnline model and it was allowed to work in parallel until it died by itself.
Basically the old Professional license allowed you to run Visual Studio Professional and be a licensed user in VSTS / Azure DevOps but being deprecated, updates or newer versions of Visual Studio (starting from 2017 and going to 2019) simply started not being able to parse that licensing info assigned to the work account for the user and the instances ended up in an Extended Trial mode.
The solution to this problem was to simply purchase the licenses from the marketplace, assigned them to all the “Professional” and after a day or two just remove the offering from the Azure Portal.
After doing the whole operation, everything licensed correctly and the issue was solved.
Signing out. Have a good one!