While setting up a new machine in the network, everything work fine, till i used the vpn. When opening outlook through vpn, it started with a password prompt, then giving an error regarding certificate, pressing ok, it would give 2 other certificate prompts, wont call it errors thought. And all worked fine. But the password prompt, and error of certificate, had to be removed. The solution was to remove the outlook profile, manually configure the users outlook profile without auto discovery. This solved the problem.
