We were still using python 2.7 waaay into 2020 - It had been heralding the impending doom since 2018 and finally end-of-lifed in 2020.

That's when I finally managed to be the loudest asshole in the room and allocate a team (myself included) to refactor shit up to 3.6 (then somewhat more modern) for a month or so.
COVID the destroyer may have helped by wrecking havoc on our client's demands pipelines.

It was the third week into "the red sprint" when my entire team (myself included) were beheaded out of the company since we had "not delivered ANYTHING in weeks!" (emphasis in the original).
Frankly, being laid off was by a large margin the best thing that company ever did for me.

I heard from a poor schmuck who stayed behind that they were still using the shitty spaghetti code from before our refactoring - in freaking November 2021 - and that our entire last effort was thrown out because "nobody knows how to use it".

There is tech debt and there is tech bankruptcy.
I may have a lot of tech schadenfreude now :)