#26759: TLSv1-only SMTP servers not supported under Django 1.9.7 / Python 3.4.4
(win32) / OpenSSL 1.0.2d
-------------------------+-------------------------------------------------
     Reporter:           |      Owner:  nobody
  RudolfCardinal         |
         Type:  Bug      |     Status:  new
    Component:  Core     |    Version:  1.9
  (Mail)                 |   Keywords:  email SMTP TLS SSL SSLEOFError
     Severity:  Normal   |  TLSv1
 Triage Stage:           |  Has patch:  1
  Unreviewed             |
Easy pickings:  1        |      UI/UX:  0
-------------------------+-------------------------------------------------
 Connecting to a Microsoft (E)SMTP mail server with the Django default
 e-mail backend (django.core.mail.backends.smtp.EmailBackend) and TLS can
 fail with the following error:

     ssl.SSLEOFError: EOF occurred in violation of protocol (_ssl.c:600)

 This appears to occur with some (more recent) versions of Python's
 smtplib, ssl (and underlying OpenSSL) with servers that only support
 TLSv1. There is no option in Django to force the TLS protocol version that
 I can see.

 The simplest illustration of failure is with:

     import smtplib
     s = smtplib.SMTP(host, port)  # port typically 587
     s.ehlo()
     s.starttls()  # fails with ssl.SSLEOFError as above

 which succeeds (with such servers) with a small modification to force
 TLSv1:

     import smtplib
     import ssl
     s = smtplib.SMTP(host, port)
     c = ssl.SSLContext(ssl.PROTOCOL_TLSv1)
     s.ehlo()
     s.starttls(context=c)  # works

 There is a suggestion of a dependence on exact OpenSSL version in the docs
 at https://docs.python.org/3.4/library/ssl.html ("Which connections
 succeed will vary depending on the version of OpenSSL...").

 Therefore, a proposed framework alternative backend is one that enforces
 TLSv1 when required, e.g. as attached. This can be selected with Django's
 EMAIL_BACKEND setting, so can be added by users, but I'd have thought that
 continuing to support such servers is important for the Django core
 project as well.

 Test software: Django 1.9.7; Python 3.4.4 (win32) using OpenSSL 1.0.2d
 (from ssl.OPENSSL_VERSION). Test server: Microsoft SMTP Server id 8.3.83.0
 (from resulting e-mail headers).

--
Ticket URL: <https://code.djangoproject.com/ticket/26759>
Django <https://code.djangoproject.com/>
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