headers in email

[Mike Cardwell]

Gregory Maxwell wrote:

>> You could set up a gmail account via tor. Then point a stunnel at
>> smtp.gmail.com port 465 over Tor using tsocks or something. Making sure
>> you have a copy of their public cert first and that the stunnel
>> validates it. I set this up and pointed my MTA (Exim) at it just for a
>> play at one point. I had to make sure Exim stripped the Received headers
>> and sent a suitably anonymous EHLO when talking to their service but
>> otherwise it worked.
> 
> It's hard to tell if your SMTP client or stunnel itself send
> identifying information. :(

I initially set Exim to freeze the messages in the queue so I could 
inspect their headers and body, to check for just this. You can then 
flush an individual message using "exim -v -M message_id" allowing you 
to watch all communication going back and forth between the two servers.

I never considered that stunnel might send identifying information of 
some sort though. Hmmm. Does anyone have any experience of using stunnel 
  with tsocks over the Tor network?

Mike