Python SSL module suddenly not found in jobs involving macOS 10.14 VMs

Question

Python SSL module suddenly not found in jobs involving macOS 10.14 VMs

Giotto Maintainers 16

After no change in my Python project https://github.com/giotto-ai/giotto-tda, my macOS CI/CD jobs are failing due to Python saying the SSL module is now missing. This had not been the case so far. We are using a strategy matrix involving three Python versions (3.6, 3.7 and 3.8) and I have noticed that the problem disappears when only one of the Python versions is kept.

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Giotto Maintainers 16

After deeper investigation, the problem seems to be due to a bad (but new!) interaction between the package manager brew and Azure. We are using brew in the step prior to the one which breaks. The default behaviour of brew is to run brew cleanup after any installation if it has not been run for 30 days. It seems that since yesterday, this corrupts something about the Python installation or its connection with the OpenSSL library. The problem disappears when I set the HOMEBREW_NO_INSTALL_CLEANUP flag to 1.

This might affect several other users so I think it would be worth investigating why it has started happening only yesterday.

kobulloc-MSFT 26,811 Reputation points Microsoft Employee Moderator

2020-10-05T18:28:36.057+00:00

It sounds like there may be a conflict with Azure DevOps and Homebrew that has been introduced recently. There are Azure DevOps specialists that will be able to investigate this further on the DevOps forums:

https://developercommunity.visualstudio.com/spaces/21/index.html
Nick Form 6 Reputation points

2020-10-27T10:21:32.103+00:00

@Anonymous I have had a thread open on this problem on the DevOps forums for six months (here). Note that the current incarnation is the second separate time we've had the problem - through experimentation I discovered that it had gone away again a couple of months after my original post but then recently it returned. No authorative answers on that thread as yet unfortunately.
Giotto Maintainers 16 Reputation points

2020-11-01T17:26:31.207+00:00

The workaround in https://developercommunity.visualstudio.com/comments/1239467/view.html is effective. This might shed some light on the nature of the issue, but I still need the 10.14 VMs... @Anonymous

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Python SSL module suddenly not found in jobs involving macOS 10.14 VMs

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