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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.

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  • You might try the Remmina mailing list also.
    – Pace
    Oct 26, 2019 at 2:44
  • @Pace How do you mean?
    – OakDEV
    Oct 26, 2019 at 18:48
  • Your question probably requires a cross between understanding how networks are different in tails and understanding how Remote Desktop protocols work. The remmina mailing list can help you with the latter. They can tell you how to debug further to get a better understanding of what is going wrong than “unable to connect”.
    – Pace
    Oct 26, 2019 at 20:27
  • @Pace sorry for gravedigging but this is an underrated comment and should be added as an answer.
    – OakDEV
    Oct 31, 2020 at 17:09
  • Some context: Tails (an operating system - "a security-focused Debian-based Linux distribution aimed at preserving privacy and anonymity.")
    – This_is_NOT_a_forum
    Nov 1, 2020 at 17:41
  • @P.Mort.-forgotClayShirky_q Gravedigging.
    – OakDEV
    Nov 1, 2020 at 17:44

3 Answers 3

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Super User seems to be the best candidate to that question, but it will need improvement to include a answerable question.

The question as written seems like an email conversation rather than a problem so focus on the problem of "Why can't I connect?" explaining what did you try so far and what the Tails development team advised you to do and why it didn't work either.

A good start is to explain why you contacted the Tails development team in the first place (error/bug?).

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  • All relevant info is included. Packets go out, don't come back. Windows machine doesn't even receive request. Error is "Unable to connect". It works from any other non-tor OS. I contacted the team to see if they understood, had leads and/or previously had heard of someone succeeding at RDPing to a non-tor machine from their OS, as it should theoretically connect. Also, as I was showering I thought of something and it works, so it's purely informational at this point. (Run hidden service on winsrv, reroute RDP port to HTTP port and connect using hiddenservice generated hostname from client.)
    – OakDEV
    Oct 26, 2019 at 5:30
  • @OakDev much clear explanation, thanks! Looks like a Windows problem so Super User is where you go.
    – CaldeiraG
    Oct 26, 2019 at 10:00
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Use the main search engine to search for [tails].

It turns that Super User has 25 results, but if you go through the list a bit further you'll find that Tor has 300. This technique applies to most "which site" questions.

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  • Security Stack has 300 "Tails" search results, along with the most tag hits and it's not the right place to ask. (Thanks for your input though, will probably try SU). Also, the question is a really specific and complex networking issue. Is there a "Network Stack" ?
    – OakDEV
    Oct 25, 2019 at 13:11
  • @OakDev There is Network Engineering, not sure if it fits your question.
    – Raidri
    Oct 25, 2019 at 13:23
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    Network Engineering won't accept this question. People are free to disagree with my advice.
    – Rob
    Oct 25, 2019 at 13:38
  • @Rob not really disagreeing, (Thanks for your input, I wasn't even aware you could search all stacks at once), but for this particular case it simply doesn't apply (as the leading stack for all my keywords is SecurityStack). Then again, a good advice nonetheless.
    – OakDEV
    Oct 26, 2019 at 5:16
  • Our Tor.SE site appears the better choice for a search using your exact question, "Remmina", or the Tag, here are two examples returned: tor.stackexchange.com/q/2048 tor.stackexchange.com/q/13915 --- the people there do accept this category of question, but we have other sites that also accept a similar question too. It's simply a matter of finding where might accept what you want to ask and has the people to answer, another factor is which site you are already a member of or you wish to join - in some cases (not this one) there are a few dozen choices.
    – Rob
    Oct 26, 2019 at 6:28
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Super User is the most likely candidate for your question. In addition to that, I would also highly recommend you to modify your question to contain an actual, answerable question.

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  • Thanks for your input.
    – OakDEV
    Oct 25, 2019 at 13:21

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