I think you raise some good points David. Regarding #1, it is currently
not feasible for the upgrader to consider configuration format changes
like that. I hope we can improve this in the future in some way, but for
now it's not really possible. The best approach is to, as Hector
suggests, read the release notes for any breaking changes between
upgrades.

Regarding #2, I think this is a big problem right now, and it almost
warrants its own bug (if there isn't one alright). There must be a clear
definition of when the upgrade is *actually* complete, and when a
rollback *really* happens.

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https://bugs.launchpad.net/bugs/2169252

Title:
  dovecot crashes on upgrade due to "disable_plain_text_auth" being
  renamed in 2.4

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