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VPN and Whonix Gateway

Hello. I have been searching endlessley on all the tutorial pages here on whonix and through previous forum threads, but I am still unable to figure a solution out for my problem.

My setup is:

Host—>VPN—>Whonix Gateway VM—>Windows VM—>VPS Proxy

The problem I have is that when I check check2ip.com or dnsleak.com.
I am regularly getting a huge list of DNS leaks from all over the world.
This is stopping me by registering on particular webites where the Captcha will never end, and not allowing me to complete personal transactions online.

Is there a simple way that I can stop these leaks coming through to my Windows VM?

  • I don’t believe the leaks are from my VPS as I have tried many other Socks5 Proxies too, with the same result.
    I thought that maybe if I were to add a VPN onto the Windows VM would work - but my PrivateInternetAccess VPN will not connect.

Would appreciate a lot if someone can help!
Thanks in advance

Good day,

sorry, but if you’re connecting to a VPS over Whonix and get DNS leaks, when using the browser in the VPS, the problem doesn’t lie with Whonix, but rather with how your VPS is configured. Adding a VPN/Proxy/Jondo or anything to your Custom-Workstation wouldn’t help you in any way, since websites you access over the VPS don’t know how you access the VPS.

Have a nice day,

Ego

I am actually using a Windows VM that has the network adapter bridged with the Whonix Gateway.
So I have just turned it into a Windows Whonix Workstation that uses an ordinary browser.
I have also tried connecting with Socks5 Proxys using a proxy client and Proxifier.

Is it not possible to implement an extra VPN along the way somewhere or any other possible way that I can browse anonymously with an extra Socks5 Proxy without these DNS Leaks?
Thank you for your reply

Good day,

sorry, but where did the VPS go, you mentioned before? Or, did you mean, you host your own proxy on a VPS you’ve rented. Because, that can lead to a whole lot of security issues. Asside from that, proxys in general, are far less capable, when compoared to a vpn solution. Either way, the problem you’re talking about now differs a lot from the one you mentioned before. Now, using a VPN in the new scenario is easy, simply install OpenVPN on the workstation. Furthermore, please keep in mind that programs like proxyfier and the concept of socks proxy’s as a whole is flawed, when comparing them to pretty much any other solution.

Have a nice day,

Ego

Sorry I may not have explained myself correctly.

My final OS is the Windows VM, where I am using a Socks5 proxy or using a hosted Proxy from a VPS.
I have just now changed some settings with the VPN and it is working.

I thought the setup was fairly safe:

Host>VPN----->WhonixGatewayVM----->WindowsVM>VPN>Socks5/VPS Host Proxy------>Internet
If everything is obtained anonymously
Maybe I am unaware of the flaws.
Thanks Ego

Good day,

without going into the technicalities, to put it simply, a proxy of any kind, is pretty much the most basic solution you can use. It doesn’t automatically encrypted your whole communication, it lacks some rather important security features, etc.

Have a nice day,

Ego

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