python2.7 pip install fails with SSLError

Steven Smith steve.t.smith at
Thu Mar 17 19:37:12 UTC 2022

Thanks everyone for your responses and suggestions.

Short story: I used the existing `sudo port install calendar-contacts-server` and … it works!

Even though this project is old and archived, I’m not aware of any open source that replaces its functionality, and it’s now fully reliant on a MacPorts stack, so I expect it will work indefinitely now.

The long story and the reason for my initial query: I had originally implemented a working instance without MacPorts, then wrote the Portfile to get a MacPorts version, then adopted the “if it’s not broke don’t fix it” attitude with my original, non-MacPorts Calendar server. So I kept that running until this week when there was some breaking change in the macOS 12.3 Python environment. I tried a quick manual install and ran into this issue, and believe I got tangled up in stuff I had to fix a couple years ago to get the MacPorts version working. IIRC the solution involves setting the correct environment variables, as done in the Portfile.

There’s one little issue I ran into, and I’d appreciate a suggested fix. The pip installer wants to see sqlparse==0.2.0 in the virtualenv, which it installs correctly, but for some reason breaks later when it finds a MacPorts-installed version of py27-sqlparse. The solution is to just uninstall this port. How should this conflict best be expressed in the Portfile?

> On Mar 17, 2022, at 15:10, Ryan Schmidt <ryandesign at> wrote:
> On Mar 17, 2022, at 04:39, Chris Jones wrote:
>> Does the port *have* to use python 2.7 ? Is it not compatible with python 3.x ?
> See where Steven asked upstream for guidance on migrating to Python 3. There was no reply. The project is no longer being developed.

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