>I wonder how "security" catches onto you. It's not legal (here anyway) to monitor every employees' Internet usage all the time. Investigating based on alerts m

>I wonder how "security" catches onto you. It's not legal (here anyway) to monitor every employees' Internet usage all the time. Investigating based on alerts may be, but what would trigger the alert in the first place? Well, as the other poster said already, in the US it is very much legal to monitor your employee's internet. As long as they're "on the clock", and/or using company resources, you can monitor them. I know for a fact that my company's proxy / firewall superbox does on the fly MitM attacks on HTTPS connections. Even though I'm connected over HTTPS right now, they're going to crack this POST open and inspect the contents, potentially even logging it, before sending it on its way. As far as how they would know about Tor, you're possibly right. They might not... to be honest I've never inspected exactly how Tor gets around the Great Firewall. However, I'm totally not risking it, as I'm 100% sure that intentional, willful bypassing of their security system in that matter is grounds for immediate termination. Maybe they don't notice it at all, maybe they can MitM Tor too, or maybe they notice via abnormal logs coming from my MAC. Either way, it's totally not worth it to me and since I have to use their hardware and their pipe, there are no guarantees anyway.