Server Version#: 1.19.5.3112
I’m able to access Free Live TV if I log in to my account on the web, but it’s not available through my Plex Server. All my home devices connect to my Plex server, so I’d like to have it available there. I’ve checked Online Media Sources in my server settings, and I don’t see it there either.
I’m not really sure what you mean by “through my Plex Server”. The web app that comes with the server, it is an older version of the web app which does not have the feature yet… The one at https://app.plex.tv is pretty much always newer than the local one that comes with server. To be clear they are both the Web app. I do not have an ETA when the one that comes with server will be updated to the same as the hosted one currently is.
The apps them selves need to support the feature, it has nothing to do with the server. A server is not required at all to use it. The current app support can be found at https://support.plex.tv/articles/free-live-tv-streaming-overview/
I have several Roku boxes with the Plex App on them, connecting to the Plex Server I’m running on a desktop PC on my local network. The “Free Live TV” option does not show up. Your explanation suggests that the clients rely on the web app bundled with the server, and that web app doesn’t yet support the option. That makes sense, and I’m fine with that. 
I’ll enjoy the feature whenever it shows up.
The web app bundled with the server is old. the feature if you decide to use it with the web app requires at least v4.38.2 of the web as mentioned in the article I linked. The bundled web app is at 4.34.4. The one at https://app.plex.tv is 4.39.1
The other clients don’t care at all what version the bundled web app is on your serve or if you have a server at all. The feature has nothing to do with the server. If you wish to use other clients you need the at least version numbers mentioned in the article.
Its possible you might have to restart a device.
I got it sorted. I’ve set up Managed Users for my devices. “Free Live TV” was not showing up as an option for them, but when I log in to my Plex server as an admin, Live TV was not included in the options under Online Media Sources. It turns out I needed to log in to my account through https://www.plex.tv in order to see Live TV as an option that I could enable for managed users in Online Media Sources. Once I did that, it showed up for the managed users on my Roku boxes.
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