So I guess you are here because you have a plugin that keeps being disabled. Well I’m pretty sure I have the solution, and as I have not been able to find the soultion for this anywhere on the internet then I decided to post it here even though this is not the stuff I usually write about.
You have probably read that you need to set the loadbehavior and that you have to set it to do not disable, and all this is true, but it does not nessecarily fix the problem as there are other settings that can cause it too. So here is a list of the things I have found need to be done to permanently fix this issue.
As this article is something that requires a bit of technical skill to understand I will not be explaining in detalil how to do each step. Also it goes without saying that you are doing this on your own risk, and of course you should backup every value before changing or deleting it.
And if you have a different Office version you of course just change the version number in the registry values below.
Start by going to the regedit
Go to \HKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Outlook\Resiliency\DoNotDisableAddinList if you see the addin here delete all its values.
Next go to \HKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Outloo.k\AddInLoadTimes and delete it here too.
If you can find the addin in Computer\HKEY_CURRENT_USER\Software\Microsoft\Office\16.0\Outlook\Addins you need to open it’s “folder” and delete everything apart from (standard).
Run outlook as an admin by pressing win+r and type in Outlook.exe /pim “new profile” and press Ctrl+Shift+Enter
Open options and press Addins.
Delete the plugin and add it again.
Go to regedit again and set the plugins loadbehavior to 3.