As a normal (non-technical) user, I used to be under the impression that adding a VPN to the tunnel length before connecting to the Tor network could only be a good thing (more encryption = more good LOL).
Now I firmly believe otherwise.
Re: Simple proxies
The wiki and Tor project docs indicate they are basically useless. Scratch that idea.
Re: Esoteric tunnels
Those built upon very small user populations e.g. I2P, probably hurt your anonymity. Scratch that idea.
Re: Tor -> VPN
The comparison table shows minimal benefits, except evading Tor bans by websites. You also can't connect to .onions and will probably be part of only a handful of people running this arrangement, which seriously harms your privacy/anonymity goals.
Plus, it is a really, really bad idea to trust you picked a non-honeypot VPN provider and that they won't abuse the permanent record of all your Tor activity at some time in the future. And so far as the 'we don't keep logs' claims, big VPN providers in the recent past have shown that promise means diddly squat.
Scratch that idea as bad based upon simple logic.
Re: VPN -> Tor
This appears on the surface to be enticing, but:
- It's not clear the ISP can't see you're using Tor anyway (I seriously doubt they can't do it, if they really wanted i.e. traffic fingerprinting);
- You now have a money trail to the VPN provider (very hard to pay anonymously);
- Increased complexity means there is a big likelihood you will stuff up something, somewhere and reduce your anonymity/security, or show your Tor activity at the network level when/if the VPN link fails;
- The attack surface is increased by running more software and providing more data flows for big brother to play with; and
- Permanent entry points into the Tor network are now limited to a MUCH smaller subset than general Tor users.
Thus this option could probably be summarised as:
- 'Might be beneficial', but Tor devs aren't convinced; and
- I can gloat about ridiculously long tunnels on forums.
But on the downside:
- It costs money;
- Hurts your anonymity on the balance of probability;
- Hurts your security on the balance of probability;
- You play Russian roulette with VPN providers;
- It's hard to set up; and
- It's easy to misconfigure.
General political comments on privacy/security goals
I imagine most Whonix users are just using this split virtualized solution to increase their default security, and/or to have greater privacy from corporate psychopaths like Google, Amazon and Microsoft who are part of the military-intelligence network now as data harvesters/profilers.
At the end of the day, if somebody's real (self-assessed) adversary is global in nature, or some blackhat who just gave a sermon at DEFCON, they shouldn't use Whonix to run a Silk Road 5.0 enterprise from home, or if they're considering dumping a treasure trove of intelligence documents.
Instead, these .000001% of users would default to TAILS from random locations. Or better yet, wouldn't use computers or electronic peripherals at all, if it is feasible in their circumstances. They'd learn about spy opsec in the meatspace, since computer hardware and software security in 2017 is useless against targeted attacks by a determined, well-resourced agency with an army of hackers, billions in funding, the law on their side, and a collect-it-all, subvert-every-protocol mentality. Lots of internet material out there on that.
The long term solution for general Tor users concerned about their inalienable privacy rights is not another protocol. Instead, it is massively increasing the population of Tor users and the size of the Tor network, and dispelling the urban myth that Tor = bad, just because some pedo somewhere is running a dodgy .onion.
All technology has potentially good and bad uses, so the propaganda is very heavy right now globally on this issue to ram through anti-democratic measures. The real aim of the power-brokers is, and has always been, control, particularly of political dissidents and reformists that threaten the status quo.