python2.7 pip install fails with SSLError

[Steven Smith]

I haven’t been able to identify the correct incantation that will point pip at a CA chain that avoids this issue, whether caused by an old LetsEncrypt cert or some other old cert.

For example, this command using --cert along with an up-to-date curl-ca-bundle (that addresses the LetsEncrypt cert issue) fails with the same error:

> pip-2.7 install --cert /opt/local/etc/openssl/cert.pem -I --user setuptools


> On Mar 14, 2022, at 9:18 PM, Jim DeLaHunt <list+macports-dev at jdlh.com> wrote:
> 
> On 2022-03-14 17:09, Steven Smith wrote:
>> I’m trying to update calendar-contacts-server to macOS 12.3. This requires installing a bunch of stuff with python2.7’s pip.
>> I’m hitting an SSLError at the command:
>>> /opt/local/bin/python2.7 -m pip install -I --user setuptools==18.5
>> Is there a way of pointing MacPorts python2.7 pip at a set of up-to-date CAs? [Say e.g. from curl-ca-bundle?]
> 
> I recall discussion recently on either the macports-dev or the macports-user lists about SSL tools failing due to expiry of Let's Encrypt certificates. I can't locate a link to those threads quickly, and I'm not sure if it applies to your situation.
> 
> Have a look at
> <https://trac.macports.org/wiki/ProblemHotlist#letsencrypt>
> 
> Is it helpful?
> 
> Best regards,
>   --Jim DeLaHunt
> 
> 

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