If my setup is Host, VPN, VM, RDP: can the data center of the RDP see my real IP address?

edited September 2017 in Mac OS X VPN Setup Posts: 10
Hi, the title says it all, 

I am just wondering what the data center that provides access to either an RDP or VPS will see regarding the IP assigned to me by my ISP. I have talked to some people who say that the data center might be able to extract one's real IP address via a debugging report on the RDP. Others have said that if one were to configure a policy audit using Group Policy Editor, which apparently can be done in the command center (?), that such would reveal the true IP address.

All of such may well be true or may just be translations lost along the grapevine, but if one's true IP is indeed able to be retrieved by a determined or even lazy data center then my question becomes, how does one go about using their VPN on their host machine such that in connecting to a VM and then an RDP, the RDP's data center can't know your true IP address? Do I need to include Tor in the equation somewhere, for example?

Thank you very much, and please don't be afraid to get lengthy if need be, long answers are indeed appreciated as getting at the root of any problems is my goal here.

Post edited by Jacksback on


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