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I saw the notice when installing Python 3.6.0b1 on Mac that said that the bundled OpenSSL is no longer used and thus 'certifi' will need to be installed and kept up-to-date.
At first, I thought, "no big deal" and pushed forward, but since, I've encountered the error in several cases:
- pip install of anything but certifi
- pip install in a new venv of anything but certifi
- distutils upload command (even with certifi installed)
I've only had 3.6.0b1 installed for a day, so I imagine I'm going to encounter new cases. Yes, indeed:
$ python
Python 3.6.0b1 (v3.6.0b1:5b0ca4ed5e2f, Sep 12 2016, 09:24:46) 
[GCC 4.2.1 (Apple Inc. build 5666) (dot 3)] on darwin
Type "help", "copyright", "credits" or "license" for more information.
>>> import urllib.request
>>> urllib.request.urlopen('https://www.google.com')
Traceback (most recent call last):
 File "/Library/Frameworks/Python.framework/Versions/3.6/lib/python3.6/urllib/request.py", line 1318, in do_open
...
 File "/Library/Frameworks/Python.framework/Versions/3.6/lib/python3.6/ssl.py", line 683, in do_handshake
 self._sslobj.do_handshake()
ssl.SSLError: [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:747)
During handling of the above exception, another exception occurred:
Traceback (most recent call last):
 File "<stdin>", line 1, in <module>
 File "/Library/Frameworks/Python.framework/Versions/3.6/lib/python3.6/urllib/request.py", line 223, in urlopen
...
 File "/Library/Frameworks/Python.framework/Versions/3.6/lib/python3.6/urllib/request.py", line 1320, in do_open
 raise URLError(err)
urllib.error.URLError: <urlopen error [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:747)>
>>> import certifi
So it seems that even the guidance of installing certifi isn't sufficient to restore the basic expectation that using the stdlib to open URLs securely.
I can't imagine this behavior is acceptable (either requiring a bootstrap step in each environment or requiring some call at runtime to set up SSL before making HTTPS calls).
I no longer have the message that the installer gave me and I don't see anything in the What's New document for 3.6 about certificates.
Is this deficiency something that's planned to be corrected for the next beta? Is there a recommended procedure to enable SSL in urllib.request?