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This topic has been discussed in a lot of places (including: here, Tor Stack Exchange, Wilders Security, ...) so I'll keep it relatively short:

"VPN over Tor" (== you >>> Tor >>> VPN >>> destination)

  • Pro: VPN provider doesn't know who/where you are (if you paid anonymously)
  • Pro: Less obstacles while surfing the web (fewer captchas and/or blocks)
  • Pro: Tor offers more creative anti-firewall measures (private Tor bridges and Pluggable Transport protocols) - although SSL/SSH-tunneled VPN usually works well too (even in places like China)
  •  
  • Con: VPN provider is able to snoop on your traffic
  • Con: It's easier for sites to track you (one VPN provider cannot provide the same anonymity pool as the bigger Tor network)
  • Con: Less flexible in most cases (pumping all your traffic through Tor first will add a bottleneck)


"Tor over VPN" (== you >>> VPN >>> Tor >>> destination)

  • Pro: VPN provider is unable to snoop on your (Tor) traffic
  • Pro: Your ISP / local admin / local network cannot see that you're using Tor (although this can also be achieved by using private Tor bridges and/or Pluggable Transports)
  • Pro: Harder for sites to track you (better anonymity pool)
  • Pro: More flexible in most cases (use Tor Browser for the web, use VPN-only for P2P, software updates, ...)
  •  
  • Con: More obstacles while surfing the sub (captchas; sites blocking Tor)

 

About P2P:

1. Please don't use Tor at all as P2P traffic generates high numbers of connections and large amounts of traffic; this unfairly strains the Tor network (and, in certain edge cases, might even defeat your anonymity).
Read:
https://www.torproject.org/docs/faq#FileSharing
https://blog.torproject.org/blog/bittorrent-over-tor-isnt-good-idea

2. That means it would be best for you to go for "Tor over VPN", meaning that you do your browsing via Tor but let your P2P applications exit directly through the VPN. This also allows you to set up VPN port forwarding for these applications.

 

3. If you're looking for anonymous P2P, take a look at the i2p network which is designed with P2P in mind. It's not as popular as Tor though, meaning fewer users, more bugs and - I would imagine - (I haven't tried it yet) slow speeds and small number of available files.


all of my content is released under CC-BY-SA 2.0

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@sheivoko

 

Adding a "Con" to VPN over Tor: all the system traffic will flow indefinitely on the same Tor circuit (for an important reason Tor does not change circuit for the same TCP stream - incidentally it is this feature that makes OpenVPN over Tor a viable option).

 

Kind regards

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