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I am considering using remote desktop protocol(RDP) over Tor, to circumvent my country's blockade of RDP and also get the most of anonymity.

I just tested a RDP connection with proxy chains remmina. (Proxy chains configured to avoid DNS leaks and resolve DNS requests via Tor instead.)

While everything was working fine technically and surprisingly the response times were quite acceptable - Vidalia warned me that the RDP connection might leak my position.

So, could you tell me how real this risk to my anonymity actually is? Should I better avoid using RDP over Tor? May there be any way to make it safe in this case?

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  • Why did you use proxychains instead of torsocks? Also, are you establishing the RDP connection over SSH?
    – mirimir
    Commented Jun 29, 2014 at 10:43

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Wikipedia says:

The RDP protocol in its default configuration is vulnerable to a man-in-the-middle attack. Administrators can enable transport layer encryption to mitigate this risk.

RDS over TLS is somewhat equivalent to https. So if you trust Tor with https traffic you can probably also trust it with RDS over TLS.

If you're dealing with proprietary software (Windows) it still might be a good idea to additionally tunnel it through an SSH connection that you know is safe.

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    Working from Debian-like VMs, I've used Remmina to access VirtualBox VMs, running on remote servers, via RDP with TLS via Tor. I've also used it to access hosted VPS via RDP via SSH via Tor.
    – mirimir
    Commented Aug 31, 2014 at 6:37

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