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Did you stabilize 18.04 over a couple days to make sure you had caught all the reconfig required? It should be no different than 18.04 > 20.04 with that step I would think. I am currently at this phase ;).

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Well, update process taking couple of days is it's own kind of nightmare.

And it wasn't my personal machine so it would've been unreasonable for me to do so.

Not always possible, of course. It's also understandable that you can't just jump through 4 years of updates in one go without some sort of work to catch up to current configs involved. I had to change 2 lines of config from 16.04 to 18.04 (due to my own tweaks to defaults), so it's been pretty pain free so far. And the few days as a precaution are on me, not Ubuntu. I should have updated years ago.

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