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Remoting from a Tails machine to a Windows one.

I have been working for a couple of days on making it work with no avail.

Using Tails with small persistent modules installed (iceweasel, remmina, proxychains & a couple others).

I contacted the small Tails dev team on their XMPP.

They asked me to document my trials and errors as it was requested a couple of times.

So basically, nothing connects.

VNC and/or RDP to the Windows machine (Both methods work if initiated from any other boxes aside from Tails)

Since I do not understand the unexpected result (cannot connect), would anyone have a clue as to WHY it does not connect?

Next step will be to setup a running Hidden Service on the target Windows machine, as suggested by Tails team.

I believe that using Tails (or Tor, as Tails mentality is aiming at an homogeneous/all-identical flow) to connect to a Windows machine could potentially bring out the core anonymity that Tails provide without the constant struggle of actually being either on Tor OR Tor>Proxy which then leaves TCP/IP OS Fingerprints from the Proxy Server used (which triggers many detection tools as abnormal)

schroeder
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OakDEV
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  • Are the Windows machine on a public accessible IP and the RDP port not firewalled? Any Tails connection will come from the public internet, so if the answer for any of those questions is *no*, that's the problem... – ThoriumBR Aug 08 '19 at 00:57
  • >(Both method works if initiated from any other boxes aside from Tails) – OakDEV Aug 08 '19 at 01:20
  • This is expected. Any other box will use LAN, Tails will use Tor and come from the internet. Unless the Windows box have public accessible IP and RDP port, it won't work. – ThoriumBR Aug 08 '19 at 02:05
  • No, any other box through WAN. I used LAN RDP/VNC maybe 2 times. Always through WAN. – OakDEV Aug 08 '19 at 02:22
  • We are not tech support and this is not a security question. You also do not include that the error message actually is, what the logs say (on both sides) or what troubleshooting steps you have performed. I'd migrate to SuperUser, but without even this basic info, I'm sure it would be closed. – schroeder Oct 21 '19 at 19:50

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