I think this is due to https://github.com/systemd/systemd/pull/30731 /
59afe07c217c73e3c7c19fb06aef2ff7bf609fd2 which was in v256-rc1.

My use case is unlocking partitions over ssh, and that commit removed
the user-early handling in that case (not necessarily intentionally; ssh
sessions get the tty type through a different branch, see
https://github.com/systemd/systemd/blob/v256/src/login/pam_systemd.c#L1033
).  There are no local gettys at this stage either, so the user-early
logic becomes not very useful.

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https://bugs.launchpad.net/bugs/2084453

Title:
  systemd 256 blocks root logins before systemd-user-sessions.service is
  up

Status in systemd package in Ubuntu:
  New

Bug description:
  In 24.10 oracular (this didn't happen in 24.04), it's impossible to
  connect to a machine before systemd-user-sessions.service is started.
  This is stricter than having /etc/nologin / /run/nologin / pam_nologin
  blocking logins, because it also applies to root logins.

  systemd-user-sessions waits for things like remote-fs.service, overall
  this makes it impossible to unlock encrypted partitions remotely or to
  troubleshoot boot issues without messing with the kernel command line
  through the boot loader.

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