Why won't my iPod connect to Mac after macOS Sequoia update?

For what it's worth - and I recognize this isn't viable for everyone - I found a foolproof workaround and have tested it on a handful of iPods: An older Mac.

At this point in time, you can get an 11" MacBook Air or 2014 or older Mac Mini for under $100 pretty easily, and apart from being potentially limited in internal storage, any machine like that - basically running older Mac OS of Catalina or earlier - will reliably maintain any iPod and iTunes Library. They run "actual iTunes" and essentially work entirely as originally designed. They won't work with newer iPhone, as far as I can tell, but my High Sierra Mac Mini connects smoothly with any iPod I can throw at it.

This is kind of a classic tech conundrum and you'll see a lot of greybeard IT guys and various kinds of organizations do it this way: keep on hand one or two machines of certain vintages to perform maintenance tasks on other devices that have been dropped by newer OSes or other software. I also keep Windows 10 and Windows XP laptops on a shelf for the blue moons when those are needed for something like decrypting an old CD. The older Macs can open things like Aperture libraries and even recover files from old versions of iMovie.

I was having the same problem with an iPod Classic 160 GB (gen 6?). I had wiped it and restored using Sequoia 15.3, but then I could only see it as an external drive. Following the Sequoia 15.4 update I was able to see the iPod in the Music App, and it prompted me to go to Finder to complete setup. Now it appears to be syncing normally.

I also changed 30-pin cables, but I don't know if that was the problem. I'll have to wait until the sync is complete to test.

I will eventually upgrade this with a new battery and storage, but it seems to be working again as stock.

Last week I was clearing my cabinets of old A/V gear for donation/recycling and rediscovered a first-gen ipod shuffle (the one with a string to hang around your neck), a newer clip-on shuffle, a 5th generation iPod Nano and 5th generation 30GB iPod. They all accepted a charge, but could not be managed on my Mac Studio that's running Sonoma 14.7.6

All are recognized as USB storage devices but ... you know the story ... Finder doesn't treat them like an iPhone.

Thanks to all the members who offered suggestions in this thread!!!

I discovered from you what seems to be the secret formula:

(1) Reformat the iPod using Disk Utility. MacOS Extended Journaled

This cleans almost everything out, leaving a basic menu but no data in the iPod.

(2) here's the secret ... Click on the iPod under "Devices" in the MUSIC APP !!!

This is where you can setup your sync settings then move selected music, audiobooks , etc. to the iPod.

The Music App threats these iPods like the good old days when we had iTunes!!! This is quite a surprise, since Apple decided that iPhone syncing should be done in the Finder.

Note about playing video on an older iPod: High Definition is not supported. You can try using a program like Handbrake to convert the HD video file to lower res, something like 320x480 or 640x480 and 30 frames per second.

It can be done. Start the restore process. When it looks like the iPod has given up restart your Mac with the iPod still plugged in. After restart do not unmount the iPod disk on the desktop. Open the Music.app and you should be right to go. Uncheck the "Enable Disk Use" & "Manually manage ..." It probably won't make any difference the iPod disk will still mount but yer whatever.

Got it working. It's possible the contacts on my 30 pin cable are performing badly due to age.

If I had two Macs, & two cables I could do conclusive all-other-things being equal tests to pinpoint the problem conclusively.

I do have two 2nd Generation Nanos, which have been helpful in this process.

I am synced now, with iPod classic and Sequoia 15.4. After several days of trying, during which I clicked "Restore", all with no result, I was suddenly asked if I wanted to reformat iPod. I said yes, then it said "synchronizing", but with no result: still no music on the iPod.. I disconnected and reconnected and then the sync ran normally. Wonderful to hear music this way again: lovely sound.

Frank It can be done. Start the restore process. When it looks like the iPod has given up restart your Mac with the iPod still plugged in. After restart do not unmount the iPod disk on the desktop. Open the Music.app and you should be right to go. Uncheck the "Enable Disk Use" & "Manually manage ..." It probably won't make any difference the iPod disk will still mount but yer whatever.

So as it turns out, it seems true what I have read on the forums that Sequoia broke the process. I was able to get hold of a Mac running Monterey, plugged in my iPod Photo and it instantly showed up in Finder like it's supposed to and all features work as they should.

Did Apple simply drop support for it in Sequoia or is it a bug????

You could try a high quality contact cleaner like this one. No doubt there may be some cleaning needed. https://a.co/d/jiqDyTV

macOS 15.4 just shipped. Update. See if it fixes the problem. No guarantees. But every update includes bug fixes as well as security fixes and sometimes new features.

Do try the full restore process as others have had success. Good luck!

There is a way to get all of your music off the iPod and into AppleMusic on your Mac.

Plug the iPod into your Mac and "Enable disk use" so the iPod mounts like any other HDD.

Click on the iPod so you can see its contents. Should be 3 folders called - Calendars Contacts & Notes

Click the "cmd" "shift" "." keys at the same time. This will reveal the invisible folders.

Navigate to the now visible but greyed out, iPod_Control : Music. In there you will find many folders called something like F00 & F44.

WITHOUT Apple Music running copy all of those folders into the Music : Media : Automatically Add to Music folder.

Start Apple Music and it will do as the folder says "Automatically Add to Music".

Apple Music will organise everything back into Artist and Albums ect.

NOTE. When I've needed to do this in the past I have always created a new Admin User, logged into it and used that with the fresh copy of Apple Music so as to not inadvertently do any harm to my music library.

Once the library is organised you can copy and add the albums your primary music library as you need.

With macOS 15.4 (Sequoia) installed, I just gave it another try:

1. connected my iPod nano (3rd Gen) with an USB-C - to 30pin - cable to my MacBookAir 2022 (M2)
2. started Music app on the Mac, iPod appeared in the app showing something along the lines "Use Finder in order to finish configuring your iPod" with a blue button "Open in Finder".
3. In Finder I restarted the configuration process, then was prompted to install a new software (1.1.3.) on the iPod, I accepted
4. Finder shows "Your Mac is trying to prepare the Software on this iPod.
5. then prompts "The connected Medium cannot be read by this computer" Options are "Reject" , "Ignore", "Initialise", I chose "Initialise", hoping the iPod would be cleaned and latest software installed
6. Finder takes me to the macOS disk utility tool, showing "Apple iPod Media" in the list on the left and underneath "disk6s2"
7. From there I can't do anything but close everything and force the iPod to unplug, I guess.... but I am going to shut off the computer and boot it up again with the iPod connected, as suggested before
8. I will come back here with further experience

Having the same problem as everyone else, figured I'd give an update re: what the situation is now that I've updated to Sequoia 15.5.

It seems to have helped; it's now recognizing that there's an iPod attached, the name of it, how much memory it has, etc; I can also look at the folders (including hidden folders with all the music in them).

However, the "sync" management page says it cannot find the device, so I can't add music.

You post implies wireless connectivity? You did connect a lightning cable to the iPod NANO 7th Gen? It should appear in Finder on the left sidebar. You need to do this at least once before you can connect wirelessly anyway. It should detect the iPod Nano and you should have an option to restore the device.

Test it on another Mac with an older macOS. Or consider creating a new APFS Volume inside the Container. Name it something like macOS instead. Download Sonoma and try that first. This creates a dual boot scenario.

How to download and install macOS - Apple Support