Most Secure Connection

Question

While there is a lot of issues concerning secure, private and anonymous Internet usage, there is little that focuses upon all the various parameters which may have a direct or even indirect bearing upon the issue.

Let us assume that I use Tails,and let us assume I use Tor on that OS. Now I have an issue with what appears to be confusing and possibly conflicting information.

If I thought that using a VPN would help me, then the information at VPN Support seems to indicate it is not advised.

If I thought that using bridges thru pluggable transports was a good idea, then I would think that I would want Tor to request a bridge automatically from a list. However, that looks like it is not possible to automate that process. At the very least, I must select a built-in bridge, even though the text states, "Unfortunately, because these bridges are publically distributed, it is easy for censors to block some of them, so some of them may not work." Oh goody!

There seems to be too many gotcha's. Exactly what is the best and most automate combination?

Answer 1

The best solution may be automated and the most automated solution may not be best. What does a bridge do? It helps to hide the fact that you are using Tor from your ISP? Do you have serious concerns about whether or not your ISP records or even cares about the fact that you are using Tor? If no, then this isn't an issue.

If yes, then it is worth taking the time to doing it right and not caring if an extra step or two is involved. Bridges are not published publicly because we don't want ISP's to block them. This is especially true when it comes to people who live in countries where Tor is outright illegal to use, so requesting them one at a time is a safer tradeoff than automation. If bridges aren't an option, there is also Project Snowflake which should give much of the same benefit without needing to request a bridge.

Answer 2

Bridges are both published, available at the tor project website, and numbering only a handful, and unpublished where handed out to individuals at request (or where individuals have set up their own bridges - don't take my advice on this).

As far as I know and have seen, bridges can be blocked on networks. I have seen tor vanilla fail, provided public bridges for obfs and seen this fail. Meek, which operates as a browser helper as far as I know, may work here, but I have also seen this fail, and have seen Tor Browser Bundle succeed where tor fails. Unpublished bridges may be another matter by all means. In all these cases, all using public wifi, it is assumed Tor is blocked, but later access may contradict this and it is unconfirmed.

I found TAILS unhelpful and problematic. The versions I used also required the user to enter bridges (from another device) and lacked built in bridges.