The outlook add-in was built back to Visual Studio 2012/2013 using .net 4. It has been working without any issue on any new machine with Office installation until Office 2016 (professional). The expect behavior is after install the add-in by running the .exe file, when first time launch Outlook, it will load the add-in and prompt to register/install in Outlook.
Recently tested using Office 365(ProPlus) machine seems stopped registering the add-in when launch Outlook. The installation folder is created in C:\Program files\, but add-in is not registered in Outlook->Files->Options->Add-ins. The work around solution is go into the installation folder in C:\Program files\XXXX Add-In\ and execute the vsto file to trigger the registration in Outlook.
I am wondering if this is something expected in Office 365 or anything I need to change/config in the installer? It didn't have any issue in the earlier version of Office/Outlook.
Thanks.