[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:           |
-------------------------+-------------------------------------------------
Changes (by isis):

 * status:  new => assigned
 * owner:   => isis
 * keywords:   => bridgedb-email, bridgedb-gsoc-application
 * priority:  normal => major


Comment:

 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.

 If the latter, the code in Twisted and pyOpenSSL for inspecting the state
 of a TLS handshake is rather gruesomely opaque, as I
 [https://gitweb.torproject.org/ooni-
 probe.git/blob/HEAD:/ooni/nettests/experimental/tls_handshake.py found
 while writing a test for it in ooni]. That said, perhaps this could be a
 very large undertaking, or possibly parts of that ooni code I wrote could
 be used (I tried to write large parts of the callbacks in a generalised
 fashion so that I'd never have to deal with this pain ever ever again).
 Perhaps we should ''force'' SSL/TLS (we shouldn't be supporting any email
 providers who don't provide SSL anyway), and refuse to send the email if
 the handshake does not succeed?

--
Ticket URL: <https://trac.torproject.org/projects/tor/ticket/10989#comment:3>
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