I am beginning to suspect this is an systemd-logind issue. I've been
thinking it's logind but just checked the upgrade packages to/from
versions and cross-checked against the changelogs.

? systemd:amd64 (237-3ubuntu10, 237-3ubuntu10.3),

And we have a major change to logind included in that:

systemd (237-3ubuntu10.2) bionic; urgency=medium

  * logind: backport v238/v239 fixes for handling DRM devices.
    These changes introduce all the fixes that correct handling of open fd's
    related to the DRM devices, as used by for example NVIDIA GPUs. This 
backport
    includes some refactoring, corrections, and comment updates. This to insure
    that correct history is preserved, code comments match reality, and to ease
    backporting logind fixes in the future SRUs. (LP: #1777099)

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https://bugs.launchpad.net/bugs/1784964

Title:
  Regression due to CVE-2018-1116 (processes not inheriting user's
  groups )

Status in policykit-1 package in Ubuntu:
  Confirmed

Bug description:
  This report is tracking a possible regression caused by the recent
  CVE-2018-1116 patches to policykit-1.

  On 18.04, since package upgrades on July 23rd, and after the first
  reboot since then on Aug 1st, I hit an issue with the primary (sudo,
  adm, etc...) user getting Permission Denied trying to do:

  tail -f /var/log/syslog

  when that file is owned by syslog:adm and is g=r.

  I then found that "groups" reports only the $USER and not the entire
  list, but "groups $USER" reports all the groups correctly.

  The user shell is set to /usr/bin/tmux and /etc/tmux.conf has "set -g
  default-shell /bin/bash"

  After changing the user's shell back to /bin/bash and logging in on
  tty1 the list of groups shows correctly for the /bin/bash process
  running on tty1.

  I investigated and found that for the affected processes, such as the
  tmux process, /proc/$PID/loginuid = 4294967295  whereas the /bin/bash
  process on tty1 correctly reported 1000. The same with the respective
  gid_map and uid_map.

  4294967295 == -1 == 0xFFFFFFFF

  The recent CVE patch to policykit has several functions where it does
  "uid = -1" which seems to tie in to my findings so far.

  I also noticed Ubuntu is still based on version 0.105 which was
  released in 2012 - upstream released 0.115 with the CVE patch.

  I suspect the backporting has missed something.

  The Ubuntu backport patch is:

  https://git.launchpad.net/ubuntu/+source/policykit-1/commit/?h=applied/ubuntu
  /bionic-devel&id=840c50182f5ab1ba28c1d20cce4c207364852935

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