Hi,
here is manual way of update:
- stop plex jail, go to program dir, in my case: cd /mnt/iocage/jails/plex/root/usr/local/share/
- rename old plexmediaserver version to "plexmediaserver.old": mv plexmediaserver plexmediaserver.old
- download latest freebsd release to that dir (/mnt/iocage/jails/plex/root/usr/local/share/) and un-compress:
tar xvjf PlexMediaServer-1.14.0.5470-9d51fdfaa-freebsd-amd64.tar.bz2
- rename created folder to "plexmediaserver": mv PlexMediaServer-1.14.0.5470-9d51fdfaa plexmediaserver
- set right owner permissions like old directory have, in my case: chown -R root:wheel plexmediaserver
- go to plexmediaserver dir and re-create missing symlinks: cd plexmediaserver/lib; ln -s libpython2.7.so.1 libpython2.7.so;
cd ..; ln -s Plex\ Media\ Server Plex_Media_Server
- Finish, you can start your jail up.