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Re: [tor-talk] Tor -> VPN Clarification



On 01/30/2015 05:27 AM, Squeak wrote:
> Hi Guys,
> 
> Thanks for the prompt replies, they are really helpful.  The image you
> posted Bill Berry was especially illuminating, thanks!
> 
> So VPN -> Tor is what I'm currently doing with Tunnelblick and TBB, but
> could somebody detail how and with which programs you would achieve Tor
> -> VPN please?    I'm having a little trouble visualising how that would
> work.

With TBB, the SocksPort is 127.0.0.1:9150. So in order to route the VPN
through Tor, you add two options to your Tunnelblick configuration:

socks-proxy 127.0.0.1 9150 /some-path/up
socks-proxy-retry

The "up" (user-password) file is undocumented, and doesn't actually need
to contain valid information, just two arbitrary strings:

foo
bar

> A follow-up question about the Tunnelblick set up, if someone does
> directly attack my connection and somehow manages to crack the VPN
> encryption they are only going to see that I'm using Tor.  Is that correct?

Yes, they'll just see encrypted connections to Tor entry guards.

> Thanks again!
> 
> Squeak
> 
> Ben Tasker:
>> VPN + Tor may also be useful if you're on a connection where you definitely
>> don't want your local ISP (or perhaps someone else on/with access to the
>> same network) to see that you're using Tor.
>>
>> In this case, the ISP may not be a BT or a Verizon, but a hotel wireless
>> provider, employer, starbucks etc.
>>
>> In that instance, the local ISP might also object to a VPN, of course, but
>> generally speaking a VPN (or an SSH tunnel) is generally seen as 'OK'.
>>
>> What you're doing there, though, is shifting the trust you'd normally have
>> for your/an ISP to the VPN provider which may or may not prove wise in the
>> long run.
>>
>> On Fri, Jan 30, 2015 at 10:30 AM, Bill Berry <bill@techwang.com> wrote:
>>
>>> This image explains VPN + tor quite well;
>>>
>>> https://vigilantcanuck.files.wordpress.com/2015/01/vpn-tor.png
>>>
>>> IMO this setup is a pretty sensible idea given the recent de-anonymisation
>>> attacks (e.g. CMU). If your Tor connection gets comprimised, all the Feds
>>> have (hopefully) is your VPN IP.
>>>
>>> The best way to set this up is VPN at a router level (e.g.
>>> http://wiki.hidemyass.com/OpenWRT_OpenVPN_Setup), then run Tails or Tor
>>> browser on your laptop.
>>>
>>>
>>> On 30/01/15 10:15, Cyrus wrote:
>>>
>>>> Squeak:
>>>>
>>>>> Hello,
>>>>>
>>>>> Relative newbie here, and I was wondering if someone could help me with
>>>>> something please. I keep seeing people describing connections to the Tor
>>>>> and is VPN connections in the following two ways:
>>>>>
>>>>> Tor -> VPN
>>>>> VPN -> Tor
>>>>>
>>>>> So if I fire up Tunnelblick, connect to my VPN provider and then open
>>>>> TBB which of the above does this describe?  And also, is there a
>>>>> recommended way of connecting these two technologies?
>>>>>
>>>> You connect to Tor through the VPN in this case.
>>>>
>>>> PC <=> Internet <=> VPN server <=> Internet <=> Tor Network <=> Internet
>>>>
>>>>  Another thing I've noticed is in the Tunnelblick client that there is an
>>>>> option to connect to a Socks5 proxy, this suggests to me that I can send
>>>>> the VPN connection through the Tor network.  But I am confused as to why
>>>>> one would want to do this, and what the benefits/disadvantages might be?
>>>>>
>>>> If you don't want a log of your actual IP, doing this would be a
>>>> benefit. Though if they already have logged where you are once as a
>>>> customer, the point of this is moot. If you had a different account, you
>>>> could then use the VPN anonymously.
>>>>
>>>>> Really appreciate any help you guys could give me!
>>>>>
>>>>> Squeak
>>>>>
>>>>>
>>>>>
>>>>>
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>>
>>
>>
> 
> 
> 
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