There are a few common reasons why some songs purchased or downloaded through iTunes may not play correctly on an iPhone. The most likely culprits include incompatible file formats, Digital Rights Management (DRM) restrictions, and syncing issues between iTunes and the iPhone.
Incompatible File Formats
The iPhone supports a limited number of audio file formats. The most common formats that work are:
- AAC (MPEG-4 Audio)
- Protected AAC (from iTunes Store)
- MP3 (MPEG-4 Audio Layer III)
- MP3 VBR (Variable Bit Rate)
- Audible (formats 2, 3, 4, Audible Enhanced Audio, AAX, and AAX+)
- Apple Lossless
- AIFF
- WAV
If you have songs purchased from iTunes prior to 2018, they are likely in the AAC format and should play fine on an iPhone. However, any songs downloaded in other formats like WMA, FLAC, OGG, etc will not play.
Solutions for Incompatible Formats
- Try converting the files to a compatible format like AAC or MP3 using a program like Apple iTunes or the free software FFmpeg.
- Upgrade to iTunes 12.7 or higher on your computer, which can natively convert incompatible formats to AAC when syncing.
- Use a third party app like SongShift to transfer songs and convert formats in the process.
DRM Restrictions
Purchased music from online stores is usually protected by Digital Rights Management (DRM) technology that restricts playback and copying. iTunes uses a proprietary type of DRM to protect its music. Songs with iTunes DRM protections can normally only be played on authorized devices or software.
If you purchased songs through other stores like Amazon MP3, Walmart MP3 Downloads, or Rhapsody, they likely have different DRM that makes them incompatible with iTunes and iPhone. Unfortunately, there is no way to legally remove DRM protections.
Solutions for DRM Issues
- For songs purchased through iTunes, authorize the computer and iPhone with the same Apple ID account used to download the music.
- Check for software updates on both devices in case DRM issues are addressed.
- For non-iTunes songs, repurchase the music on iTunes which will give you DRM-free versions.
Syncing Problems Between iTunes and iPhone
Improperly syncing your iPhone to iTunes is another common reason for songs not transferring correctly. Here are some things that can disrupt the syncing process:
- Connecting multiple devices to the same iTunes library
- Allowing apps like Spotify access to your iTunes media folder
- Having “Sync Music” disabled in iPhone settings
- Storing your iTunes library on an external drive
- Sync interruptions due to computer errors
These types of issues can lead to missing or incorrectly matched songs when syncing. Carefully managing your sync settings and library folders can help.
Fixing Syncing Problems
- Only sync one iPhone device to your iTunes library
- Disable media access for third party apps like Spotify under settings
- Check that “Sync Music” is enabled on your iPhone’s summary tab in iTunes
- Consolidate your iTunes library on your computer’s local drive
- Use the “Transfer Purchases” option to redownload missing songs
Corrupted or Missing Files in iTunes Library
On occasion, the original song files in your iTunes library can become corrupted or go missing from the folder location on your computer. When this happens, iTunes will be unable to find the file to sync to your iPhone.
Possible causes include accidentally deleting files, changing file locations, drive errors, and application conflicts. Using iTunes’ Library management tools can help identify and restore missing files.
Fixing Corrupted/Missing Files
- Go to File > Library > Organize Library to consolidate and check for errors
- Use Show Duplicates option to help find copies of missing songs
- Check iTunes folder location for accidentally deleted files
- Use Library > Find Duplicates to search your computer for song copies
- Redownload any purchased songs that cannot be located
Incorrect iTunes Account on iPhone
If you have songs purchased under multiple iTunes accounts, it’s important to sync each iPhone to the matching account. If you accidentally have mismatched accounts, purchased songs will not transfer.
To check this, go to Settings > iTunes & App Store and verify you are logged into the account originally used to buy the content. You can also check account under iTunes summary tab.
Fixing Mismatched iTunes Account
- Go to iPhone Settings > iTunes & App Store and sign out
- Sign back in to the proper account that purchased the missing songs
- Disable Automatic Downloads to prevent unintended downloads
- On your computer, authorize iPhone with the same account used for purchases
Issues with iOS Version Compatibility
Major iOS updates like iOS 7, iOS 11, and iOS 13 have been known to cause issues with opening and playing songs purchased under previous software. This is because the updated Music app and media playback system is not always backwards compatible.
Updating to the latest compatible iOS version can resolve most playback issues. However, very old songs may require an alternative player app to function properly after significant iOS updates.
Solutions for iOS Compatibility Problems
- Update iPhone to the latest available iOS software via Settings
- Toggle on iCloud Music Library to re-upload songs
- Use a third party media player app for incompatible formats
- Convert incompatible songs to more modern AAC codec
Insufficient Storage Space on iPhone
In order to properly sync purchased songs, your iPhone needs sufficient built-in storage space available. High capacity devices like the 128GB/256GB iPhone models are recommended.
If you consistently see “Not Enough Space” errors when syncing, it’s likely your iPhone does not have enough free space left. This will prevent full libraries from transferring over successfully.
Making Space for Music
- Check iPhone storage under Settings > General > Storage & iCloud Usage
- Delete unused apps, messages, photos/videos
- Disable Automatic Downloads for new music purchases
- Use iTunes to manually transfer selected playlists or albums
- Upload your library to iCloud and stream songs as needed
- Upgrade to a higher capacity iPhone model
Conclusion
Troubleshooting song syncing between iTunes and iPhone can be tricky, but is usually caused by one of several common issues like incompatible formats, DRM restrictions, sync conflicts, missing files, account mismatches, iOS compatibility problems, or insufficient storage. Taking methodical steps to isolate the specific cause and applying the appropriate fixes will typically get your music library back in sync.
Some key troubleshooting tips include checking for incompatible formats, consolidating your iTunes library files, ensuring proper account matching, updating to current iOS versions, clearing space by removing unused apps/media, and using wired iTunes syncs to transfer purchases and playlists. With patience and care, you can get iTunes and iPhone working harmoniously together.
