I assume the affected system is a live USB/installer system? It is not
quite obvious from the description.

I am having the same issue of missing logrotation when using the Ubuntu
Desktop 14.04.3 LTS installer
(http://releases.ubuntu.com/14.04.3/ubuntu-14.04.3-desktop-amd64.iso) as
basis for a demonstration/test setup.

Seeing my logs accumulating I tried to configure logrotate but was
puzzled when seeing it already configured and cron seems to run
cron.daily according to log (.1 is caused by me running logrotate
manually):

ubuntu@ubuntu:~$ grep cron.daily /var/log/syslog* 
...
/var/log/syslog.1:Jan 11 06:25:01 ubuntu CRON[19057]: (root) CMD (test -x 
/usr/sbin/anacron || ( cd / && run-parts --report /etc/cron.daily ))
/var/log/syslog.1:Jan 12 06:25:01 ubuntu CRON[20265]: (root) CMD (test -x 
/usr/sbin/anacron || ( cd / && run-parts --report /etc/cron.daily ))
/var/log/syslog.1:Jan 13 06:25:01 ubuntu CRON[21361]: (root) CMD (test -x 
/usr/sbin/anacron || ( cd / && run-parts --report /etc/cron.daily ))

Digged a lot to find out /usr/sbin/anacron was intentionally diverted
using dpkg-divert, but haven't found out yet if and how this affects the
cron.daily execution;

ubuntu@ubuntu:~$ dpkg-divert --list|grep anacron
local diversion of /usr/sbin/anacron to /usr/sbin/anacron.distrib

ubuntu@ubuntu:~$ ls -l /usr/sbin/anacron
lrwxrwxrwx 1 root root 9 Nov 18 14:11 /usr/sbin/anacron -> /bin/true

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https://bugs.launchpad.net/bugs/1385537

Title:
  logrotate does not rotate logs (rsyslog)

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