Sorry for such a technical question but I’ve actually researched this and so I don’t know how else to ask it really. First, please allow me to be as specific as possible so as to avoid misunderstandings.
Here is the set up I’d have in mind:
Whonix > VPN > tor > VPN > RDP.
When I have asked people about whether a data center that rents out the RDP would be able to resolve one’s true IP address (the IP address assigned to the user by their ISP), I have asked it within the context of a VPN being on, then a classic virtual box being accessed (not Whonix), and then the RDP.
In that context, which is of course clearly different than the configuration asked about here, the answers vary.
Some people say it depends on the kind of RDP and that there is basically no way to tell.
Others say, no the RDP host (for example the data center that rents out the RDP) will not be able to see the true IP address of the client connecting remotely to the desktop. Instead, they say, the RDP host will only be able to resolve the VPN IP address.
Others are clear: the RDP host will be able to see the true IP address regardless of the VPN’s being on so as to encrypt the data.
Other IT buffs tend to dismiss the question in assuming that it’s blackhat stuff and that they don’t want to be involved. Some ask me why I would want to do such a thing as to ensure that the machine I am connecting to can’t resolve who I am. My question though is only about whether the host of the RDP would be able to see the MAC or host name or IP address of the client if the client were using both a VPN and a virtual box. So, sadly, the answer doesn’t seem as simple as the question.
Here though, my question is more about the Whonix set up available to us and its use in conjunction with an RDP. Does anyone know if with said configuration (again, Whonix > VPN > tor > VPN > RDP) one can be protected from the RDP host or whether the host will still know the true IP address?
Some people have said that a VCN would provide end to end encryption, but others have told me that the RDP host will still be able to see the true IP address and that such is only a means of accessing an RDP if within the RDP they have turned on a VPN service. So lots of conflicting information and I’m not sure where to look if to be sure.
Thank you for reading and any help you may offer.