I had the same experience when upgrading rsyslog [rsyslog:amd64
(7.4.4-1ubuntu2, 7.4.4-1ubuntu2.1)]. I manually added:

 # use the syslog group by default, since this is the owning group
 # of /var/log/syslog.
 su root syslog

To top of the /etc/logrotate.conf, which resolved the problem.

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https://bugs.launchpad.net/bugs/1278193

Title:
  logrotate skip the rotation of many files under /var/log due to bad
  group ownership

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