Ok I gave up trying to fix this. Cron to the rescue.
sudo crontab -e
Then add the following line to the super user's crontab
# Logrotate they said...
3 6 * * *               /usr/sbin/logrotate -f /etc/logrotate.d/derp &> /dev/null
 The -f flag forces logrotate to rotate the logs. The file located at /etc/logrotate.d/derp is the corresponding logrotate configuration for my application.
Its ugly, but it was the only way I could fix this bug. Hope this helps someone.