How do I troubleshoot the "There is an error with this item" error with syncing?

Plex Players Mobile Devices
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Server Version#: 1.19.5.3112
Player Version#: 8.3.1.19108

I replaced the SD card on my Samsung Galaxy S8 with a larger capacity card (SanDisk 128GB Extreme MicroSDXC UHS-I Memory Card). Because of that, I needed to re-sync all my Plex media to it.

All the movies I wanted on there synced without a problem as did most of my music playlists. However, I have two music playlists that I just can’t seem to get synced. On two of them (“She’s Gone Country” and “JJ-1”), it syncs some of the music and then errors out with “There is an error with this item.” Right now, I’m troubleshooting the “She’s Gone Country” playlist to sync since it only has 206 songs on it.

I’ve seen the complaints and I know that sometimes the Sync feature can be a little finicky. I’m Ok troubleshooting it, but I just need to know how I should be troubleshooting. If it’s a problem with certain music files, which ones? I don’t mind re-ripping them. If it’s another issue, what’s the problem? The error is too generic to figure out the next step.

I’ve attached the logs so I’m hoping you can point me in the right direction on what I should be doing to troubleshoot. Also, which log file contains the info on syncing?

For some additional info, I have the Plex Server running on its own PC with 8GB of RAM. It’s less than a year old, has plenty of free space, and runs great otherwise.

Plex Server:
180GB free on the C drive where Plex is installed
1.09TB free on the D drive where all my media is located

Samsung Galaxy S8:
27GB free on the main storage where the app is installed
80GB free on the SD card where Plex syncs my media to

As a side note, I have exact copies of the playlist under two other profiles on the server and was able to sync it to their devices without a problem.

Any help would be much appreciated! Thanks!

– Jim

Plex Media Server Logs_2020-07-27_14-00-10.zip (6.7 MB)

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Hoping to bump this up - thoughts anyone?

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I have the same problem. I’m trying to sync a couple of playlists to my phone to listen to music offline, and a lot of them will not sync, but it just displays a generic “There is an error with this item”. I exported a “debug file”, but I don’t know what to do with it. Any help is appreciated. I switched to Plex from Google Play/YouTube Music and now I can’t really listen to anything on my phone… Very disappointing.

When attempting to play the “sync’d” playlist, the app displays “there was an error playing this item” and the app completely crashes and restarts, forcing me to then pick my account again and returns me to the home page.

Now when I try and go into the playlist and click the down arrow to sync the playlist, it gives me an error saying “Sync is a premium feature and requires the associated server to be signed in with a Plex Pass enabled account” - The server is signed in with a plex pass enabled account…

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I had the same problem. Fixed it by removing all devices (except servers) from the Devices list in Plex, and then reinstalling the Plex app. This happens every few weeks though, and is extremely annoying. Had a post on Plex unable to sync to mobile iOS devices which describes it further.

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