test_ssl fails on OS X 10.10.2 with latest patch level of OpenSSL libs

[ned-deily]

BPO	23345
Nosy	@pitrou, @ned-deily

^{Note: these values reflect the state of the issue at the time it was migrated and might not reflect the current state.}

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GitHub fields:

assignee = None
closed_at = <Date 2015-02-05.06:28:13.346>
created_at = <Date 2015-01-29.02:04:12.722>
labels = []
title = 'test_ssl fails on OS X 10.10.2 with latest patch level of OpenSSL libs'
updated_at = <Date 2015-02-05.06:28:13.344>
user = 'https://github.com/ned-deily'

bugs.python.org fields:

activity = <Date 2015-02-05.06:28:13.344>
actor = 'ned.deily'
assignee = 'none'
closed = True
closed_date = <Date 2015-02-05.06:28:13.346>
closer = 'ned.deily'
components = []
creation = <Date 2015-01-29.02:04:12.722>
creator = 'ned.deily'
dependencies = []
files = []
hgrepos = []
issue_num = 23345
keywords = []
message_count = 6.0
messages = ['234935', '234956', '234957', '234961', '235419', '235420']
nosy_count = 3.0
nosy_names = ['pitrou', 'ned.deily', 'python-dev']
pr_nums = []
priority = 'critical'
resolution = 'fixed'
stage = 'resolved'
status = 'closed'
superseder = None
type = None
url = 'https://bugs.python.org/issue23345'
versions = ['Python 2.7', 'Python 3.4', 'Python 3.5']

[ned-deily]

With the latest maintenance release of OS X 10.10 (10.10.2), the OpenSSL libs have reached a patch level that fails the sanity test in test_ssl:

test_ssl: testing with 'OpenSSL 0.9.8zc 15 Oct 2014' (0, 9, 8, 28, 15)
under Mac ('10.10.2', ('', '', ''), 'x86_64')
HAS_SNI = True
OP_ALL = 0x 7ff
[...]
======================================================================
FAIL: test_openssl_version (test.test_ssl.BasicSocketTests)
----------------------------------------------------------------------

Traceback (most recent call last):
  File "/py/dev/3x/source/Lib/test/test_ssl.py", line 309, in test_openssl_version
    self.assertLessEqual(patch, 26)
AssertionError: 28 not less than or equal to 26

Is there anything special about 26 or can the value just be bumped?

[pitrou]

The assumption was that the patch level represented a letter (from 'a' to 'z'), but we can certainly relax that.

[pitrou]

Er... OS X 10.10 ships OpenSSL 0.9.8??

[ned-deily]

Yep, 0.9.8 is the newest and presumably last major of version of OpenSSL in OS X. OpenSSL has been officially deprecated by Apple in OS X since OS X 10.7; it's only there for third-party products shipped by Apple in OS X, like Python. Their own apps use Apple's own frameworks like SecTransform and CommonCrypto. (See, for example, http://rentzsch.tumblr.com/post/33696323211/wherein-i-write-apples-technote-about-openssl-on) Apple also ships 0.9.7 shared libs in 10.10 for really old applications.

[python-dev]

New changeset 49f07942fbd7 by Ned Deily in branch '2.7':
Issue bpo-23345: Prevent test_ssl failures with large OpenSSL patch level
https://hg.python.org/cpython/rev/49f07942fbd7

New changeset 52932cd7f003 by Ned Deily in branch '3.4':
Issue bpo-23345: Prevent test_ssl failures with large OpenSSL patch level
https://hg.python.org/cpython/rev/52932cd7f003

New changeset 62b322b82f00 by Ned Deily in branch 'default':
Issue bpo-23345: merge from 3.4
https://hg.python.org/cpython/rev/62b322b82f00

[ned-deily]

Fixed for 2.7.10, 3.4.3, and 3.5.0.