I know my boss could potentially see what sites I visit when I'm at the office if he would want to because I'm connected to the office WiFi or wired connection.

But what about when I'm at home on my own network and I have a VPN connection to the office? Tunnelblick is used for that on my OS X machine.

I think my main issue is that I don't know exactly how the VPN works. I only know that with it I can reach certain websites and svn repositories that are local to the office network. Is every http connection routed to my office or something? Or does it just change my IP maybe? Tunnelblick keeps track how many MB is received and send through the VPN and I'm curious how that exactly works as in how does it know what needs to be send over the VPN, but maybe that's another question on its own. My main concern is whether my boss can see my browsing behaviour that way.

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1 Answer

There is no absolutely sure way, to find out. Because there might be some software installed on your system, that always tracks your actions.

But you can find out, if your Traffic runs through the VPN.

Just visit whatsmyip.org with and without VPN, and compare. If it's the same IP, it looks like your traffic is not affected by the vpn.

If it's different, it's going through your vpn.

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