I think there is still an issue with Update Art and pick a poster. Based upon what I am seeing, I believe there may be a maximum number of episodes where it just fails and does not change the art of any episode or the show itself. In testing, I have not been able to narrow in on an exact number, but have determined it is not number of seasons that seems to make it fail. The only consistency I can see is that it takes longer to run when there are more episodes and at some point it just straight up fails if there are too many episodes. Even if I do not chose to propagate to the episodes, I cannot change the main poster if there are a lot of episodes. This happens both with Stream Links and personal media.
On my Up Next I am seeing the December 31, 1969 again in Library / Up Next with latest tvOS beta.
Another thing I have noticed is that on other "specials " shows (not series), there is a "show" tag marked in the Categories metadata (from recorded programs on the DVR) that is missing in the edit metadata dropdown. I am able to select and add the other tag "special" that appears in all these one off specials I record. I am getting the series menu instead of the immediate popping up of the episode due to the missing tag. The last image as an example.( my guess)
FWIW, After time, some of these episodes seem to load without the series menu.
I have yet to try my sports recordings, but I am loving this so far!
Yes, this is because it has neither an Episode Title nor an Original Air Date, so it's trying to use the recording date, which is empty, hence that date.
I'll work on auto populating the original air date based on the created at date for the file for unscanned items. For now, if you want to fix this, give it an Original Air Date or Episode Title.
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I had an air date in the metadata. I had titles in there at first but it listed it twice on the screens and I thought I was supposed to leave it blank. 
EDIT: I do see how editing a title fixes that issue. Maybe the solution is if the special has the show + special metadata tag that it will pull title data from the episode name from the show's inserted meta data field? Currently, (I'm guessing) it's duplicating that field as its looking for a show name and episode name.
This has frustrated me also, some tv shows just will not apply any art work change in my local library.
I thought I would check your theory out, alas I have a tv show with 39 episodes spanning 4 seasons where the artwork changes fine. But another tv show with 25 episodes spanning 3 seasons where the artwork will not change. Both tv shows are stored on the same external HD, identical file permissions. Just cannot figure out a pattern.
Fixed in the latest dvr pre-release.
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This was a LIE! Sorry guys. This hadn't been merged in yet. That's why I thought I "forgot" to mention it 
. It'll land eventually though.
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This new feature is working great. I'm really enjoying being able to incorporate more of my older media library, tagged nicely into Channels DVR's unified interface. The possibilities now feel (even more) endless...
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This is a UI request that would help anyone editing a very long list of newly imported media like I am. The Edit Metadata window could use a "Save & Next" button, or perhaps a keyboard shortcut, that achieves the the same result (save the edit, and advance to the next recording's metadata window.) This was a big time-saver when I was editing MP3 tags in iTunes back in the day. Managing without either of those means lots of mousing and clicking around.
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Is it expected behavior to lose the show artwork when you edit metadata for an episode?
DVR > Manage > Shows
Bunch of fixes in the latest build:
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Can you replicate this on latest build? If you don't check that box, it should finish almost immediately.
This is fixed now.
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YES, YES, YES!
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This is awesome! Thank you @Maddox @tmm1!
I updated to v2022.03.04.2327 and images load and show on my Mac. Uploaded images showing up as blank purple box on AppleTV beta. Didn't see a new build in TestFlight. Anything I need to do to see the images?
Questions on importing Specials. Like a documentary.
Importing as a flat TV Show.
Many of mine end up getting automatically mismatched when imported as a flat TV Show and there is no correct match available. In order to import them, I have to choose the closest match and edit the metadata/poster.
Question here is since the closest match I select has a gracenote series id and tms show id, my understanding is the DVR will not record this if it ever airs, since it sees it already imported. So the closest incorrect match I chose would be considered already recorded, correct?
Importing as a Movie.
Same thing, have to find the closest match and edit. Same question.
The latest pre-release has a button to remove the match for movies.
We’ll work on doing the same for an imported show.
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Was really excited about this ans just tried it this morning. I had some shows created with non standard urls in the 4:3 areas. On the clients, these actually were displayed, but perhaps not in the greatest quality.
Just updated the libraries with all home grown 4:3 artwork.
They appear perfect in the web server. However, in the clients they are now blank. Do i need to refresh something somewhere?
Also something i noticed that may be an issue once music videos and home videos are supported more down the road.
It would also be very nice to add local import of the 16:9 and 4:3 aspect ratio images for the collections, and the virtual channels logos to keep in line with the local import for the metadata editor.
This is exactly what im seeing too. Didnt see your post and just posted the same thing…
Can i ask how people have the folder structure for these kind of files? Eg i have approx 30 random football videos from the internet. I have these in a single folder under imports/TV/ but when scanning it probably takes about 5 minutes per episode for each to finally appear in my library. So for all 30 is going to take well over an hour before they have all been added into channels for me to then edit the metadata etc.
Is there anything i'm missing or is it just that each episode takes a while to be scanned before Channels ultimately decides it cannot find a match and moves onto the next?
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What does the Log show about those files?