New submission from Christian Heimes:

Hostname verification makes not much sense without verifying the certificate 
chain first. At the moment one has to set verify_mode to CERT_REQUIRED first:

>>> import ssl                                                                  
>>>                                                                             
>>>                                                                             
>>>                                                                           
>>> ctx = ssl.SSLContext(ssl.PROTOCOL_TLS)
>>> ctx.check_hostname, ctx.verify_mode                                         
>>>                                                                             
>>>                                                                             
>>>                                                                           
(False, <VerifyMode.CERT_NONE: 0>)

>>> ctx.check_hostname = True
Traceback (most recent call last):
  File "<stdin>", line 1, in <module>
ValueError: check_hostname needs a SSL context with either CERT_OPTIONAL or 
CERT_REQUIRED
>>> ctx.verify_mode = ssl.CERT_REQUIRED
>>> ctx.check_hostname = True


On the other hand verify mode cannot be set to CERT_NONE without disabling 
check_hostname first. One has to remember to set the values in opposite order!

>>> ctx.verify_mode = ssl.CERT_NONE
Traceback (most recent call last):
  File "<stdin>", line 1, in <module>
  File "/home/heimes/dev/python/cpython/Lib/ssl.py", line 485, in verify_mode
    super(SSLContext, SSLContext).verify_mode.__set__(self, value)              
                                                                                
                                                                                
                                                                  
ValueError: Cannot set verify_mode to CERT_NONE when check_hostname is enabled.
>>> ctx.check_hostname = False
>>> ctx.verify_mode = ssl.CERT_NONE


I find this confusing. In order to support PROTOCOL_TLS_CLIENT with 
_create_unverified_context(), I had to modify the code to this abomination:

    if not check_hostname:
        context.check_hostname = False
    if cert_reqs is not None:
        context.verify_mode = cert_reqs
    if check_hostname:
        context.check_hostname = True

Rather than making our users to jump through additional hoops, check_hostname = 
True should just set CERT_REQUIRED. This is a sane and safe default. On the 
other hand, ssl.CERT_NONE shall *not* disable check_hostname and still fail 
with a ValueError if check_hostname is enabled.

By the way we should not suggest CERT_OPTIONAL here, too. For TLS client 
connections, CERT_OPTIONAL is not really optional. CERT_OPTIONAL: 
SSL_CTX_set_verify(ctx, SSL_VERIFY_PEER, verify_cb), CERT_REQUIRED: 
SSL_CTX_set_verify(ctx, SSL_VERIFY_PEER | SSL_VERIFY_FAIL_IF_NO_PEER_CERT, 
verify_cb). According to 
https://www.openssl.org/docs/man1.0.2/ssl/SSL_CTX_set_verify.html 
SSL_VERIFY_FAIL_IF_NO_PEER_CERT is ignored in client mode. I'll open a new bug 
report.

----------
assignee: christian.heimes
components: SSL
messages: 301967
nosy: christian.heimes
priority: normal
severity: normal
stage: needs patch
status: open
title: SSL: check_hostname should imply CERT_REQUIRED
type: enhancement
versions: Python 3.7

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Python tracker <rep...@bugs.python.org>
<https://bugs.python.org/issue31431>
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