Hi, I think the mentioned changes should be documented using debconfig and unless the administrator answers „yes, do as I want“ the upgrade should be aborted. Otherwise many systems will silently upgraded to an unbootable state as for example in Bug#847119 .
BTW. It looks to me that the corresponding functions should be implemented in one place for all packages together (cryptsetup, systemd etc.) so that they cen honour the following cases: nested /usr (with subdirectories) bind /usr symlinked /usr Tobias
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