How many tv shows are you expecting to see in On Deck currently?
Keep in mind that there is also this server setting, which can severely limit the number of items in On Deck, when set too low:
Your above screenshot shows that you currently have one half-played episode in Continue Watching. The next episode of this tvs show won’t appear in On Deck until you have watched the in-progress episode completely (or set it to “watched” manually).
I was expecting at least 2 which I know have been added in the last few days. I haven’t messed with those settings so they should be there.
I also created a throwaway account, signed into an incognito window, shared libraries with my plex server then skipped through a show to add something to the on deck menu and it does show up but it’s definitely broken in some way
when i click “what’s this?”
Could you please just drag your screenshots into the message editor of this forum?
(copy & paste of graphics is also possible)
There’s an old glitch that I don’t think has ever been fixed. If Continue Watching and On Deck are exactly equal, then On Deck doesn’t show. Try watching a few minutes of a movie, (which won’t appear on Deck, because it’s a movie) and see if it makes a difference. That fixed it for me a few months ago. 
EDIT: It also gives you the “Content Unavailable” message for on deck if the conditions above are met.
Edit 2: On Deck - Content Unavailable
oh sorry i didn’t know i could do that
whoa that actually fixed it for the throw away account and for my main account (when i watched a movie on the main account as well).
Not sure why the new episode of my hero academia didn’t show up in “on deck” though and still isn’t. I have “Include season premieres in On Deck” enabled and that’s a show that I’ve been keeping up to date with but this is definitely good enough.
Thanks to both of you for helping me figure this out
Yeah, I’m not sure why they never fixed that bug.
I’m guessing it’s a precursor to combining “on deck” and “continue watching” and they didn’t want to have both features showing the exact same content
Good that it’s sorted.
I totally forgot about this bug. It wasn’t fixed because it is very rare and practically only affects new user accounts.
Don’t think so. That was way back in Sept of last year, but they may have been working on combining things behind the scenes then.
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