How to manually update Plex in a FreeNAS jail

Pre-Update Steps
Login to the servers as root

Download the update to the server

1) change to the plexmeduaserver directory

root@plex:/ # cd/usr/local/share/plexmediaserver

2) stop the plexmediaserver service

root@plex:/usr/local/share/plexmediaserver # service plexmediaserver stop
Stopping plexmediaserver.
Cleaning up leftover child processes.

3) Copy the plex update to the current directory

3) Unzip the Plex update (the exact name of the update will be slightly different to what is shown

root@plex:/usr/local/share/plexmediaserver # tar -zavf PlexMediaServer-1.16.6.1592-b9d49bdb7-FreeBSD-amd64.tar.bz2

4) Check it looks like it is suppose to (optional)

root@plex:/usr/local/share/plexmediaserver # ls PlexMediaServer-1.16.6.1592-b9d49bdb7
CrashUploader
Plex Commercial Skipper
Plex DLNA Server
Plex Media Fingerprinter
Plex Media Scanner
Plex Media Server
Plex Relay
Plex Script Host
Plex Transcoder
Plex Tuner Service
Resources
lib
start.sh


5) Copy everything from the newly created folder to the current folder (the exact name of the folder will be slightly different to what is shown)

root@plex:/usr/local/share/plexmediaserver # cp -r PlexMediaServer-1.16.6.1592-b9d49bdb7/* .

6) Start the service again

root@plex:/usr/local/share/plexmediaserver # service plexmediaserver start
Starting plexmediaserver.

7) Check the service status

root@plex:/usr/local/share/plexmediaserver # service plexmediaserver status
plexmediaserver is running as pid 5859.