python2.7 pip install fails with SSLError

[Jim DeLaHunt]

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