2.7 was end-of-life in 2020! And Python 3 outdates 2.7 by a few years.

A company using 2.7 in 2022 is an indicator that the company as a whole doesn't really prioritize IT, or at least the project the OP worked on. By 2017 or so, it should have been clear that whatever dependencies they were waiting on originally were not going to receive updates to support python3 and alternative arrangements should be made.

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icedchai 3 days ago | parent [-]

You captured the fundamental issues. There were mountains of technical debt. I recall encountering a dependency that had not been updated in over 10 years.

	▲	Izkata 3 days ago \| parent [-]
		We have VB deployments that haven't been changed at all in about that long. Finally got approval to do a rewrite last year, which is python 3.6 due to other dependencies we can't upgrade yet. It got this bad because the whole thing "just worked" in the background without issues. "Don't fix what isn't broken" was the business viewpoint.