I have a question that was originally posted on the security Stack Exchange site, but it turns out the issue would prove to be more relevant to a network stack.
What is your opinion / where should I ask this question:
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 of 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, using Remmina to initiate a connection from Tails to a Windows Machine (No hidden services, clear net) results in a "Unable to connect" message.
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? I can ping the machine && remoting to it from any other OS works like a charm.
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)
Questions: Has anyone ever successfully made a RDP connection from a Tails to Windows setup? My packets go out but don't come back (Unable to connect) Works from any non-tor bridged/routed OS.