Troubleshooting

What to do when an iPod doesn't appear, gets ejected, won't sync or eject, when songs are missing from the iPod, and other common problems.

Most problems have a quick fix. Find yours below. If a sync goes wrong, ClassicTunes says what happened in plain words, and Details on the iPod's page shows the full log.

#Run iPod Diagnostics first

When an iPod is acting up, choose iPod › Run iPod Diagnostics… (or click Run Diagnostics… on its page). It checks:

Each check that finds a problem says what to try. See iPod tools.

#The iPod doesn't appear in ClassicTunes

ClassicTunes sees an iPod when macOS mounts it as a disk that has the iPod's music folder (iPod_Control) on it.

1. Check Finder. If the iPod isn't in Finder's sidebar either, macOS hasn't mounted it, so ClassicTunes can't see it.
2. Try another cable and port. Plug the iPod straight into the Mac rather than through a hub or keyboard. Old 30-pin cables wear out, and many charge without carrying data.
3. Wake the iPod. Make sure it's turned on and isn't low on battery; let a flat iPod charge for a few minutes first.
4. Put the iPod in disk mode. On a click wheel iPod, reset it by holding Menu and the center button until the Apple logo appears, then immediately hold the center button and Play/Pause until "Disk Mode" appears. Then connect it.
5. Check the model. iPod touch, iPhone, iPod shuffle and the iPod nano 5th and 6th generation aren't supported. A shuffle or nano that does appear shows a "not supported" banner on its page, and syncing is turned off. See Supported iPods.

If the iPod appears in Finder but not in ClassicTunes, quit ClassicTunes and open it again with the iPod connected.

#"Your iPod Was Ejected" right after connecting

Finder ejects an iPod a few seconds after it connects when Finder manages it. To keep it connected:

1. Select the iPod in Finder's sidebar.
2. On the General tab, turn off "Automatically sync when this iPod is connected".
3. Turn on "Enable disk use" (or "Manually manage music").
4. Click Apply, then reconnect the iPod.

While ClassicTunes is open, it also stops other apps from ejecting an iPod in its first moments after connecting and while it's syncing.

#"This iPod isn't supported yet"

A red banner on the iPod's page means the model needs a database signature ClassicTunes can't produce yet, so syncing is turned off. See Supported iPods.

An orange "Experimental support" banner means syncing works but the model hasn't been tested yet. If ClassicTunes couldn't identify the model from its SysInfo file, syncing should still work for click wheel iPods, but album art may not show. For an experimental model, take a snapshot first (Take Snapshot on its page) so you can put the iPod back as it was. See Snapshots.

#A sync fails

ClassicTunes explains what went wrong and what to try. The common messages:

macOS's own message is kept in the sync's Details, if you need it.

#Songs are missing from the iPod

• Apple Music songs. Songs from an Apple Music subscription are copy-protected, and no iPod can play them. Import from Music App… lists them as "Apple Music (protected)" and they can't be imported. iTunes Store purchases, CD rips and your own files import normally.
• Songs only in iCloud. In Import from Music App…, songs that live only in iCloud show as "Not downloaded". Select them and click Download in Music, and they become ready once the Music app has fetched them.
• Audible audiobooks. Audible's copy-protected .aa and .aax files are skipped with a message, because they can't be played or synced.
• Not chosen. Check the iPod's Sync Options: it syncs the entire library or only the music you chose. See Syncing.
• Didn't fit. Preview Sync… lists songs left off and how much more space is needed. See Preview Sync.

#Songs in other formats

You don't need any extra software to sync FLAC, Ogg Vorbis, Opus, WMA and other formats: ClassicTunes includes what it needs to read them, and converts anything the iPod can't play during the sync (to AAC, or Apple Lossless for lossless songs). Videos are converted to a format the iPod plays.

To convert songs once instead of at every sync, use iPod › Find Songs iPods Can't Play…. It also finds songs saved in a layout the iPod can't read, or with sample rates above 48 kHz. See Tidying up.

#The iPod won't eject

• "ClassicTunes is syncing this iPod." Wait for the sync to finish or cancel it, then eject.
• "ClassicTunes is reading this iPod." Try again in a few seconds.
• "The iPod is in use, so it couldn't be ejected." If Finder is showing the iPod (or a message about it), close that first, then try again.

Right after a sync, macOS sometimes still has files open on the iPod, so ClassicTunes keeps trying for a few seconds before saying it couldn't eject.

#Songs already on the iPod appear twice

After you forget an iPod (or use one that was synced by another library), the next sync copies every song again, and songs already on the iPod are kept as well, unless Remove items that aren't in this library is turned on in its Sync Options. Turn that on and sync again to remove the extra copies. See Syncing.

#ClassicTunes opened the wrong library

Each iPod belongs to one library, and plugging it in opens that library. To pick a library yourself, hold down Option while ClassicTunes opens, or choose File › Library › Choose Library…. See Libraries.

If ClassicTunes says "Can't Switch Libraries Yet", an iPod is syncing, a CD is being imported, or songs or podcasts are still being added. Try again when it's finished.

#"Library Not Found"

ClassicTunes can't find the library's folder, usually because it's on an external drive that isn't connected. Connect the drive and click Try Again. Locate… lets you find the folder if it's moved, and Use Default Location… starts with the library in the default place instead (the missing library isn't affected). Both restart ClassicTunes.

#A CD imports with problems

If part of a track can't be read, ClassicTunes retries, and tells you if a stretch is still unreadable. Clean the disc (wipe from the center outwards) and import it again; re-importing replaces only the damaged songs. See CDs.

To stop the Music app opening CDs as well, set "When you insert a music CD" to Ignore in System Settings › CDs & DVDs.

#The Play key still opens Music

• Turn on Open ClassicTunes when the Play key would open Music in Settings › General › Play key.
• The key only comes to ClassicTunes when no other player has it. If another app was playing, the key goes to that app.
• To stop Music opening at all, turn on Always open ClassicTunes instead of the Music app.

#No notifications

Notifications only appear while ClassicTunes is in the background. If they're turned off in System Settings, Settings › General › Notifications says so; click Open Notifications to turn them on.

#ListenBrainz didn't accept the token

Copy your user token again from your ListenBrainz settings (Open ListenBrainz in Settings › Scrobbling takes you there), paste it and click Sign In. If ListenBrainz couldn't be reached, check your internet connection; plays wait and are sent when the Mac is back online. See Scrobbling.

#Snapshots won't save

Snapshots can't be kept on the iPod itself. Choose another folder in Settings › Backups › Where snapshots are kept. A full iPod can take a long time to copy the first time; later snapshots only copy what changed. See Snapshots.

#"Updates Aren't Available Yet"

Copies of ClassicTunes made before its release can't check for updates. See Updates.

#Still stuck?

Check the FAQ, or choose Help › ClassicTunes Website.

If that doesn't help, email support@classictunes.app with your iPod model, your version of macOS and what happened; the Support page lists what helps.

#From AppleScript and Shortcuts

Scripts can check what a sync would do, and back up an iPod before syncing it:

tell application "ClassicTunes"
    if (count of iPods) is 0 then return "No iPod is connected."
    preview sync iPod 1
end tell

In Shortcuts, use Preview iPod Sync and Back Up iPod. See AppleScript and Shortcuts.