So today I thought it would be a good idea to mess up things that were not broken 
I installed FreeNas on my server. Then installed PLEX on that and now I am wondering
how Do i add media. Does Plex have FTP built into it and if not how do I make it so I can
upload media via FTP to my plex media directories??
Thanks for the Help in advance.
You would set up a share (AFP/SMB/NFS/FTP, whatever your preference is), and then upload the media to the server. You would have to link the media directory in the Plex jail to the location outside the jail you are keeping your media, and the user and/or group “plex” would need read rights at least to that directory. Note: Plex’s user/group ID is 972.
So here is what I found in case anyone is looking for the FTP way in to add files
FTP into FreeNas then find directory under tree , make your directory you want to put movies etc in and then upload to that directory.
I really think PLEX needs to build in a FTP server to it’s software. I would make sense as there is no real way to ADD media from a remote location without it.
I’m not sure how you set up your vdevs, but your method is going to result in uploading directly to the jail drive. In most setups you’ll run out of space real fast.
Plex’s design is tuned to the idea you have local in-person access on the machine it’s running on, like a Windows machine where you can just point Plex to your normal Videos/Music/Picture folders or drag and drop stuff into the default folders in the setup. Same if it were a Linux desktop. Running it on a headless system has always required additional work by the owner to set up the media.
Part of your complaint is an issue with FreeNAS’s design philosophy. FreeNAS has always been meant to be a network attached storage product and only used on a LAN, they even actively state so in the forums. Being able to run plugins at all is a more recent addition. The issue is they openly advertise plugins like Plex and NextCloud that function as webservers and require external access to take full advantage of while creating FreeNAS with data security and resiliency as the core focus.
Personally I have the Plex user and group added to the FreeNAS system itself and a user account of my own name. Then I set up mount points on the jail leading to directories on normal storage pools. I also map those same directories as SBM shares, which I set the ACL on the share as my own username as the owner, and Plex as the group, with permissions set to Inherit. Then I mapped those shares as a network drive on my PC, set to autoconnect on login.
What this means is my Plex library folder are for all intents and purposes an extension of my normal PC’s filesystem:
I don’t have to launch a client to access them, or even log in. They are just there for me to copy to and delete from freely, and with “plex” as the group Plex Media Server can interact with them, too.
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