[tor-bugs] #10989 [BridgeDB]: bridgedb should use starttls for outgoing mails

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#10989: bridgedb should use starttls for outgoing mails
-------------------------+-------------------------------------------------
     Reporter:  arma     |      Owner:  isis
         Type:           |     Status:  assigned
  enhancement            |  Milestone:
     Priority:  major    |    Version:
    Component:           |   Keywords:  bridgedb-email, bridgedb-gsoc-
  BridgeDB               |  application
   Resolution:           |  Parent ID:
Actual Points:           |
       Points:           |
-------------------------+-------------------------------------------------

Comment (by sysrqb):

 Replying to [comment:3 isis]:
 > Sysrqb, if I recall correctly, you looked into this at the 2014 Winter
 meeting... did you discover anything notable?
 >
 > I do not recall off the top of head if emails sent out from BridgeDB are
 sent through Postfix, or directly sent from the `bridgedb.EmailServer`
 module.

 It is the former, and so far it seems to be doing what we want. I was
 silly and assumed it was the latter when I talked to arma. I just tested
 the inter-operation with yahoo.

 yahoo -> bridges.tp.o:
 {{{
 Received: BridgeDB
 From xxxx at yahoo.com  Fri Mar  7 XX:XX:XX 2014
 X-Original-To: bridges at bridges.torproject.org
 Delivered-To: bridgedb at ponticum.torproject.org
 Received: from nm36.bullet.mail.ne1.yahoo.com
 (nm36.bullet.mail.ne1.yahoo.com [98.138.229.29])
       (using TLSv1 with cipher DHE-RSA-AES256-SHA (256/256 bits))
       (Client did not present a certificate)
       by ponticum.torproject.org (Postfix) with ESMTPS id
       for <bridges at bridges.torproject.org>; Fri,  7 Mar 2014 XX:XX:XX
 +0000 (UTC)
 Received: from [127.0.0.1] by nm36.bullet.mail.ne1.yahoo.com with NNFMP;
 07 Mar 2014 XX:XX:XX -0000
 Received: from [98.138.100.113] by nm36.bullet.mail.ne1.yahoo.com with
 NNFMP; 07 Mar 2014 XX:XX:XX -0000
 Received: from [98.138.226.160] by tm104.bullet.mail.ne1.yahoo.com with
 NNFMP; 07 Mar 2014 XX:XX:XX -0000
 Received: from [127.0.0.1] by omp1061.mail.ne1.yahoo.com with NNFMP; 07
 Mar 2014 XX:XX:XX -0000
 Received: (qmail 58298 invoked by uid 60001); 7 Mar 2014 XX:XX:XX -0000
 Received: from [162.243.119.77] by web126103.mail.ne1.yahoo.com via HTTP;
 Thu, 06 Mar 2014 XX:XX:XX PST
 X-Mailer: YahooMailWebService/0.8.177.636
 }}}

 So it appears to be unencrypted intra-yahoo, but `TLSv1 with cipher DHE-
 RSA-AES256-SHA` over the net. Not bad.

 bridges.tp.o -> yahoo:

 {{{
 From bridges at torproject.org Fri Mar  7 XX:XX:XX 2014
 Return-Path: <bridges at torproject.org>
 Received: from 127.0.0.1  (EHLO ponticum.torproject.org) (38.229.72.19)
 by mta1311.mail.ne1.yahoo.com with SMTPS; Fri, 07 Mar 2014 XX:XX:XX +0000
 Received: from ponticum.torproject.org (localhost [127.0.0.1])
 by ponticum.torproject.org (Postfix) with SMTP id
 for <XXXX at yahoo.com>; Fri,  7 Mar 2014 XX:XX:XX +0000 (UTC)
 Content-Type: text/plain
 From: bridges at torproject.org
 To: XXXX at yahoo.com
 }}}
 SMTPS is used during the return, so its security level is not immediately
 obvious but it's still better than plaintext.

 And, in addition to cypherpunks' post,
 gmail -> tp.o uses `TLSv1 with cipher ECDHE-RSA-RC4-SHA`

 Also, for the record,
 tp.o -> bridges.tp.o uses `TLSv1.2 with cipher ECDHE-RSA-AES256-GCM-
 SHA384`

--
Ticket URL: <https://trac.torproject.org/projects/tor/ticket/10989#comment:5>
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