I’m facing challenges playing back synced/downloaded content on my iPad. I’m able to actively stream from my Plex server to the iOS app, but when I try to play (or have preference set to prefer downloaded content), I receive an error stating “couldn’t create the playback session for this item.” And when trying to view synced content, I see “iPad is currently unavailable” where I’d normally see my local content.
I don’t get much from the client on the “why” it’s unable to play, so any advice on debug for that would be appreciated.
My (admittedly old, but still very capable as a video player) iPad is running iOS 9.3.5 and Plex App 6.7.2. When I tried to sync new content this past week (which I’d not done for a LONG time), I found issues with the Let’s Encrypt certificate and iOS not providing new root key updates. I added the ISRG root key by using Safari to go to https://letsencrypt.org/certs/isrgrootx1.pem installing the certificate/Profile/Trust on the iPad.
This was successful in allowing me to connect to my Plex server just fine and I was able to sync content to the iPad again, which I had been unable to do before installing the Profile. I can also stream content from my Plex server to the iOS app with no issues (no connection errors, etc.)
Could this be related, in any way, to the new root certificate profile? I tried setting my PMS Secure Connections to Disabled with no change. I wasn’t surprised this didn’t change anything, as I doubted it had anything to do with synced content or connection to the PMS, but more likely something certificate related or similar for the local iPad.
I understand the device is old. I understand Apple no longer supports it. I understand there are no new Plex app updates for something that old. I get all of that, and the only thing I use the iPad for, really, is to take entertainment with me when I’m at the gym, or on an airplane. All this is said just to avoid the “you should upgrade your device” comments that will likely come anyway. 
Thanks!
