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Some music won't transfer to iPod Touch

I am one of those people who still uses my iPods for certain situations. Much prefer them to using my iPhone for music in these contexts. When I buy new music on the iTunes store (again my preference), I can download most files to my iPod Touch also, and transfer them to my other iPods.


However, I have some music files on my iMac that are, for example, songs written and played by my son. I want these also on my iPod Touch. When I try to transfer them manually through the Music program (dragging them over from my library window of Music when it is open on my iMac to the icon of the iPod in the left pane of the Music program) sometimes the transfer is successful, and sometimes not. A song will show up in the Song list of the iPod on the iMac screen (when I click on the the iPod icon in the left pane of the Music program open on my iMac), but not appear in the Library on the iPod itself. It seems arbitrary whether it works or not.


Any ideas? Very frustrating.

iPod Touch (6th Gen)

Posted on Apr 2, 2022 8:37 PM

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4 replies

Apr 2, 2022 8:52 PM in response to DanG77

You may want to consider subscribing to Apple's iTunes Match service.

Tunes Match uploads your music library from the Apple Music app on your Mac or iTunes for Windows on your PC. Then you can access your music library on all of your devices that have Sync Library turned on.

Subscribe to iTunes Match - Apple Support


iTunes Match can significantly reduce the amount of manual intervention needed to synchronize your music library across multiple devices. The current cost of an iTunes Match subscription in the US is $24.99 per year.


iTunes Match will let you selectively downloads tracks you have stored in the cloud to avoid issues revolving around managing limited storage space.


Please be advised that iTunes Match is not a back up service and you should back up your music regularly.



Apr 4, 2022 9:59 AM in response to DanG77

I bridle a bit at paying for an extra service

That's completely understandable.


Based on your requirements and the moderate complexity of your device echo system, I don't think there is an obvious or straightforward solution to your challenges. That said, with a bit of effort, it likely is possible to manage your music to your specifications across all of your devices.


If you don't mind sharing this information, I have a few questions for you.


  1. How many devices are you using to manage your music?
  2. What is the age and model of each device you're using to manage your music?
  3. Which operating system is installed on each device?
  4. In what format is the music created by your son saved (e.g., .aiff, .wav, .alac, .mp3, etc.)?


I would check to make sure you're running the latest version of iOS/macOS on each of your devices. Some older versions of Apple Music may not support the format your son's music is saved in.


iTunes Match gives you access to your entire music library from any device, regardless of whether or not that music exists in a public database. You can rip a CD, add metadata to it, and iTunes Match will ingest the music and treat it as a part of your overall collection.


If you add your son's music to an Apple Music library with iTunes Match enabled, the tracks will be uploaded to iCloud. Any metadata and artwork associated with the tracks will be uploaded to iCloud as well. The same music will then be available to all of your devices for download on a per track or per album basis (from any device).


Music in your Match collection that has not been downloaded will be visible with a cloud icon indicating that you can download it to your current device.


iTunes Match was one of the better decisions I've made concerning managing my music library. It turned an oftentimes tedious and manual library management process into a largely automated exercise requiring little intervention on my part. My entire music library (including non-iTunes tracks), containing some 10,000 songs, is available to any of my devices via iCloud. I download the albums and or tracks I wish to have locally on my device to avoid streaming over cellular or WiFi networks. This arrangement makes the question of which device my music is on almost irrelevant. Any device I sign into has access to all of my music regardless of whether or not I purchased it from Apple.


Apple will also swap your low-res tracks for higher quality files for music you didn't purchase via their service (if the music is available in Apple's library). I've always thought that was a nice perk of the service.


I hope these notes prove somewhat helpful, best of luck to you.

Apr 4, 2022 7:57 AM in response to BrotherEye

Thanks for the response, and recommendation. I bridle a bit at paying for an extra service to restore functionality that should be basic to the devices, and that has always worked reliably until now. It still sometimes seems to work, and sometimes not, which is so frustrating. I like having manual control because I have a fair amount of music in my iMac Apple Music library that I don't want on any of my iPods. So I don't want to have to be constantly removing music from the iPods after they sync. And a fair amount of the music is not available on any web based service. The other issue is that we live in a place with unreliable internet access or cell service. So I want the actual song files on my iPod to be able to listen to them... not stream from my library on a web based service (though perhaps iTunes Match allows this?).


I was able to get this last song over via a manual file transfer, and it now shows in the iPod Touch music library. However, it does not have the "album artwork" which is not something available for download, as this is a "home recording."


Hoping there is some kind of obvious simple solutions.

Apr 6, 2022 9:17 AM in response to BrotherEye

Thanks for your response, and for more information on iTunes Match. I will consider it.


The devices I use are: 27 inch iMac Late 2013 OS 10.15.7 (latest available for this generation, getting long in the tooth), iPod Touch 6th Generation (last produced with the latest IOS version available for it, 12.5.5), and believe it or not I still use my iPod Classic (in my studio) and an iPod Shuffle for workouts. The last two still allow me to manually drag songs, or albums over to them (in the left pane) of the Music app when they are connected to my iMac.


The iPod Touch has been the difficult one... working sometimes, but sometimes not with manual transfer. I can download songs to it that I buy on the iTunes Store, no problem. I do have over 13, 000 songs on it (and this is just a small portion of my music). So it could have been an issue of space, though it seemed to have 2.5 gigs of free space on it.


I did figure out a work around, or a solution though for now. On the iPod's window in the Finder on my iMac (when it was mounted, obviously), first, in the General window, I deselected "Automatically Sync" and selected "Manual Manage" which had been selected before anyway (though it seemed to revert to "autosync" by default. Then I went into the Music pane (menu) and selected "Sync" and "Manually Manage". I went through and selected all the artists I wanted (leaving out some borderline to save space), and selected the two Playlists that were critical to me. Bit of a pain, but so it goes. Shift or command clicking doesn't allow you to select multiple artists. You have to select one at a time. Then I hit "apply". Took a bit, but not too long, and everything including artwork and artists that I manually put on my iMac were transferred, including my son's music.


Hurray!


Thanks again. I'll consider the Match service.

Some music won't transfer to iPod Touch

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