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You can always have both in parallel. The first one to test changes and deploy to production and the second one to try to upgrade your dependencies. Should all the test pass on the second one, you can then commit the new requirements.txt and other updated package versions.

You can then run the second continuously and warn when it fails and handle whatever happened manually, without having a broken prod.

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we do that but it's hard to CI a whole operating system, some week ago we got bit by a weird imagemagick bug that was triggered by very specific tiffs that weren't in out test suite but that one of our clients used extensively for their product images.

annoying and wouldn't have happened if we were running pinned versions, that said getting stuck on old software would be worse. however nothing can ever test something like that fully, just too many combinations :(

Yup software will always break. The key is whether you can fix it quickly (fix meaning land commits AND get it in prod) and test for the issue in an automated way in the future.

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