Two issues, possibly related:
1. Using the “Import from iTunes” feature to update my playlists with “Overwrite existing playlists” checked removed most of them.
I have just over 150 playlists in iTunes right now, most of which were reflected in Plex due to previously importing/syncing them. When I most recently re-imported from iTunes to Plex yesterday using the Playlists “Import from iTunes > Overwrite existing” option, Plex now has only 37 playlists. They’re a seemingly random selection of the ones in iTunes (I can’t find any pattern: some are older and some newer; some are from earlier alphabetically and some later), and many (most?) of them are missing at least some tracks.
2. Even manually importing missing playlists doesn’t always import them correctly.
There’s one playlist in particular that I was trying to correct (along with syncing newer playlists), which is a cut-down playlist of “only” 11 hours of Christmas music (216 songs). After being manually imported from an M3U file, the version in Plex is just shy of 9 hours long (175 songs, i.e., missing 41 songs). I thought it might be an issue of file formats not being supported by Plex (though I was pretty sure everything was MP3), so I searched for one song that I knew for sure was missing, and I found it in Plex, was able to play it, and was able to manually add it to the playlist in Plex itself. (These missing songs are the entire reason I did a refresh on the iTunes playlist sync to start with, thinking that I must have just synced an earlier version of the playlist.)
Does anyone know what’s going on here or how to solve it? The idea of having to manually re-create a gross of playlists (some of them very long) literally song-by-song inside Plex is maddening.
Server Version#: 1.30.0.6486
Player Version#: Plex Web 4.97.3 & random others
Edited to add: I’m manually reviewing the M3U vs. the playlist right now, and not only are there files missing, but so far there’s at least one file added that isn’t currently on the playlist (the same song is on there twice, but from two different compilations). It may have previously been included but later been removed. I have tried importing the file under slightly different names to see if it made a difference (e.g., if Plex were somehow getting confused by an older cached version with the same name), but that didn’t fix anything, so I’m stumped.
ETA2: Created an entirely new version of the playlist with a unique name by creating a playlist in iTunes from the files of the current playlist, exported that as an M3U, and imported it into Plex: same missing files, same extra file(s).
ETA3: Made sure the XML file was up to date via iTunes menus, then tried importing again. Now I just get this error: “Something went wrong. Make sure the server is available and try again.” Edited again: But while giving the error, it seems to have actually imported all the playlists this time (albeit with still some missing files on some playlists).
