-----Original Message-----
From: Tom Eastep [mailto:[email protected]] 
Sent: Wednesday, 8 May 2013 11:26 AM
To: [email protected]
Subject: Re: [Shorewall-users] Transparent Proxy

On 5/7/13 5:29 PM, [email protected] wrote:
> On Sunday, May 05, 2013 06:57:49 AM [email protected] wrote:
>>
>> I have a Tor gateway set up, and would like to route all traffic through it. 
>>  For security, different functions should use different Tor ports, so they 
>> have different virtual circuits.
>>  
>> I've assigned port 9110 to be the port for email.  My mail client uses SSL 
>> for email (POP3s: 995, sSMTP: 465), and I want to direct all accesses to 
>> from those ports through the Tor SOCKS port of 9110.  This should mean that 
>> the mail client sends an email out 465, which is then tunneled by Shorewall 
>> (somehow) to 127.0.0.1:9110, and out the Tor network to the exit node, where 
>> it then proceeds to the mail server listening on 465.
>>  
>> Anyone know how I would do this in Shorewall?
> 
> Anyone have input on this?  
> 
> Or has Benny Pedersen poisoned the well for me?

Firstly, Is the mail client socks aware? If it is not then that is the issue 
you need to fix. If it is, then tell it to use the socks proxy on port 9110

Shorewall is an IPTables configurator, it is NOT a proxy. Shorewall isn't a 
magic bit of software that knows how to interface to a socks proxy.

You need a socks aware email client. 

Using IPTables to redirect SSL traffic to a transparent proxy is a method that 
will guarantee to break every secure connection. If you get into the habit of 
accepting broken certs, then you are less, not more secure.

SSL and TLS need explicit proxying, not transparent proxying by IP redirect/nat 
into a waiting proxy. Down this path thar be dragons.

I hope this helps.

T

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