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Our Company is using a TMG (Threat Management Gateway) server to grant the employees access to the internet. It's not strict and users can make VPN connections and use the proxy extension of Chrome as well.

If a user uses a VPN connection to access another server outside through this TMG server and uses the Chrome proxy extension would it be possible for a server admin to log the visited URLs of the user?

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A HTTP proxy server doesn't hide the content of the connection, it simply makes the request on behalf of the requester. Now, if you're tunneling that through a VPN before it reaches the TMG server then your traffic should not be readable by the TMG (assuming the VPN is configured correctly e.g. DNS leaks, WebRTC, etc.).

With that in mind, it's usually pretty easy to tell that a VPN connection is being used on the network, and if that's against policy you could get in trouble for that.

There could also be additional software that was installed on your devices (assuming these are company devices) which are logging your browsing.

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