I used to update my port of plexpass in FreeBSD by stopping my jail, and entering the following:
pkg update && pkg upgrade
portsnap fetch update
pkg upgrade plexmediaserver-plexpass
pkg install plexmediaserver-plexpass
This use to work just fine, but at some point along the way the port stopped updating. I have since updated my FreeNAS installation to v11 (stable), but this did not help. I have tried forcing pkg update and pkg upgrade, but this just reports back that the packages are all up-to-date.
I am currently running v1.3.3.3148 of plexpass, but according to freshports, the newest version is v1.8.0.4109.
Here is the link for the freshports page: https://www.freshports.org/multimedia/plexmediaserver-plexpass/
Any help would be greatly appreciated
After a lot of digging I found an answer. Because my jails was from a very old version of FreeNAS (BSD), the template was out of date and not able to be updated. This is a known issue and there are several bugs reported to FreeNAS and FreeBSD. I found one forum post that helped discover the issue but was not able to resolve the problems.
I decided to create a new jail, install my packages from scratch and move the metadata over. After dealing with some permission issues with the moved metadata, I got everything working correctly. Packages are now updating, plexpass is working and all my metadata is in tact. Here is the post that helped me find my issue:
https://forums.freenas.org/index.php?threads/keeping-the-jails-up-to-date.20062/