First and foremost the support professionals at WatchGuard have no interest in in taking my calls or emails. My employer is vested in WG firewalls but since the VPN issue is mine and not common to the company I have to deal with it and I’m not likely to get the support contract number or serialno. From that perspective WG is just not my friend.Chromebook’s VPN assumes (a) your certificates have been publicly blessed by a CA (b) using the VPN port and NOT 443 as is most common place. Getting past these limitations means a lot of manual labor. Here are some of the links I have been accumulating:Chromebook VPN Setup (link)convert PEM to key file (link)Chromebook and OpenVPN server (link)And yet it still does not work.