Quick answer
Rename the file to something under 255 characters total, including the full path on the device, then re-sync. That's it. If it still fails, the device's filesystem (usually FAT32) enforces a 255-character limit per file, and WMP doesn't trim names automatically.
Why this happens
What's actually happening here is that Windows Media Player builds a destination path on your portable device, and that path—drive letter, folders, and filename—exceeds the filesystem's maximum path length. Most devices use FAT32, which caps individual file names at 255 characters. WMP doesn't truncate automatically; it just bails with NS_E_PDA_RETRIEVED_FILE_FILENAME_TOO_LONG (0XC00D1240). This usually shows up when you're syncing files that came from a CD rip or a download with a super descriptive name like “Artist - Album - 01 - Track Title (Live at Venue, 2023) [Remastered].mp3”. That's easily 80+ characters, and the folder structure on the device adds more.
The error can also pop up if you're syncing a file from a deeply nested folder on your PC. WMP copies the relative path, so a file buried in Music\Lossless\Live\2023 ends up with a long path on the device too.
Fix steps
- Find the offending file. In WMP's sync list, right-click the file that shows the error. There's no direct way to see the filename length in the list, so note the title and locate it in your library.
- Rename the file on your PC. Right-click the file in Windows Explorer, select Rename, and shorten it. Aim for under 50 characters. Keep the artist and track name, ditch the rest. For example, change
Artist - Album - 01 - Track Title (Live at Venue, 2023) [Remastered].mp3toArtist - Track Title.mp3. - Resync. In WMP, right-click the file and choose “Sync”. The error should be gone.
- If the error persists, shorten the folder path on the device. Some devices create folders like
\Music\Artists\ArtistName\AlbumName\. That eats into the 255-char limit. Use WMP's sync settings to change the folder structure. Go to the Sync tab, click “Sync options”, and set the folder name to something short, likeMusiconly.
Alternative fixes
If renaming every file feels like a pain, you can bypass WMP entirely. Drag and drop the file directly onto your device in Windows Explorer. Explorer handles long filenames more gracefully—it will still fail if the name is over 255 chars, but you'll get a clearer error and can rename on the spot.
Another option: use a different sync tool. MediaMonkey and MusicBee handle long filenames better because they let you set a custom filename template that truncates automatically. I've used MediaMonkey for years, and it never throws this error.
If you're on a Windows 10/11 machine, you can enable long path support via Group Policy or the registry. This fixes PC-side path limits, but it doesn't change the device's filesystem limit. FAT32 is FAT32, so don't expect a miracle.
Enabling long paths in Windows only affects the OS's own path handling, not the device's filesystem. The 255-char limit on FAT32 is hard-coded in the device's firmware.
Prevention
The real fix is to stop creating monster filenames. Set your ripping software (or download script) to use a shorter template. In Windows Media Player, go to Options > Rip Music and change the filename format to something like Artist - Title. That prevents the problem at the source.
Also, if you're syncing a lot of files, check the device's file structure periodically. Some devices create hidden folders that push path length over the limit even with short filenames. Keep an eye on the sync log—WMP records the exact path when it fails, so you can see what's eating the characters.
One last thing: on some Zune-era devices (yes, they're still out there), the limit is 200 characters, not 255. If you're stuck with one of those, you'll need even shorter names. Test with a 200-char filename to see if that's your threshold.