There doesn’t seem to be a problem with Plex recognizing that a track is number 1000, but after 999 the track number field starts at 100 because it can only show three digits. Simply adding the capability to show four digits in the track field would fix it.
Which app, and where are you seeing this? In playlists on Plex Web, at least, it shows more than 1000 tracks with no trouble.
I’m on Plex Web on Chrome for Mac. Could it be a setting I’m missing?

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I don’t know of any setting that would do that. Is it a playlist or an album detail page? I don’t have any albums that big.
It’s a collection of an old time radio show that had 1400 episodes, which is why they’re all in one folder. Bummer it doesn’t work. All they’d need to do is increase the max in the track field from 3 digits to 4 and all would be right.
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