Sorry, I figured out what was going wrong in my specific case just after sending the last message. Turns out it are not all my users whose files and directories are group-writable - only mine.

The users are meant to be able to read one another's files on the shared machines by default, so they're all in the same group. But they're not meant to be able to read all the sysadmin's files, so my primary group is a separate group with the same name as my login name. What I intended as an extra layer of protection turned into a liability when upgrading to trixie. Because I often share files with users by issuing "chown :joint-group some-file", and this is a bit of a problem if the files are unexpectedly group-writable...

Lesson learned: letting the behavior of file access permissions depend on comparing a login and group name is prone to cause surprises, if not security-critical edge cases. At the end of the day, the impact of my case is limited, but this is a change I wouldn't confidently push out into the world if I were managing a popular Linux distro...

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