MSP here using endpoint protection.
Problem 1 -
For some reason my Webroot clients never update, on any computer. I always have to install the latest WRSA.exe installer manually. This has been going on for over a year.
Problem 2 -
I installed the latest, 18.104.22.168 a few minutes ago. Upon inspecting the WR log files, I found that Webroot is blocking itself when updating/installing.
Blocked: Webroot Process ""C:\Program Files\Webroot\Core\WRSkyClient.x64.exe"
Have you opened a ticket and sent this over to support? Our enterprise support are going to be who can help you diagnose and resolve this issue