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

The main use for an older iPod in 2025 is the same as it would have been in 2001, playing music.

Primarily, playing my music. Not the music on someone else's computer through a cloud service. Not whichever version of the track Apple wants to supply today instead of the track I purchased on iTunes in 2004.

There are in fact people out there who are sick of paying the same price as buying an album every month, and finding that their "favorites" will "randomly" vanish from "library" if not played often enough. People tired of saving a playlist with 100 carefully curated tracks, only to open it five years later and see that it mysteriously contains now only 30 of those tracks.

These are things that don't happen with a "plain old fashioned iPod."

I am also having this issue with my iPod 3rd gen after installing Sequoia where it does not show in Apple Music.

It seems it will sync the iPod just once after a laborious restart but then will not recognize it - that is not good. My music library and iPod are the major reason I have my Mac Mini so I am very interested in the solution. It seems like an issue that can be fixed - if Apple focuses on fixing it.

I use a new, licensed, iPod classic as part of my live performance setup ... Playing break music between sets. Yes, I'm old. 77 currently and I still perform as a single or duo act (with a Lady singer). I have been a full time, professional guitarist and singer for over 50 years. Mostly in the Northern Nevada casino scene. I use backing tracks that I create in my own studio, and my current studio setup is quite up to date. I've been using Macs since 1992, starting with OS6. My current rig is a 2023 MacBook Pro, with the M3 chip, 2 TB storage, 36G RAM, and I currently own and use Reason 13 as my DAW software. (if you wish to hear or view my work, go to rfrankjones.com) I'm trying to update my iPod contents to add the new tracks I'm using for part of my live act, aside from my performance tracks. I have just given in to moving up from Sonoma to Sequoia, and this with not being able to make the iPod work with Sequoia has totally destroyed the iPod. Sonoma worked fine ... you people at Apple have completely forgotten the Purpose of Macintosh computers starting with OSX. We were always able to set up and work our desktops to suit our personal wishes and styles.

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I eventually got my 2nd Generation iPod Nano connecting to Sequoia 15.4. I can relax with my tunes with my old case & lanyard. Occasionally, someone notices I'm putting an old device to good use.

But, you're using your iPod professionally. A current iPhone will be more reliable. Just be sure to put it into airplane mode when using it on the job. Low power mode will help the batter last longer.

You can still have fun with your iPod offstage!

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

I was syncing my ipod 4th gen up until two weeks ago and now suddenly it says 'The selected device could not be found'!

Where are you guys finding any 'restore' function? I can't click on anything, it's greyed out and it's just spinning until I get that error message.

I have a brand new 30pin to USB cable...

Edit: and by the way it works fine as a hard disk, and shows up in the sidebar both as a hard disk and ipod but it's only the syncing music that does not work...

I really hope this can be fixed!!!

Just upgraded to 15.5 last night and my iPod Mini still gets "failed to recognize" error after spinning for 2 mins.

For what it's worth, I am able to sync with other USB connected iPods on the mac (a stock 1st gen Mini and a 1st gen Nano). The issue is with my "daily driver" which is a 1st gen Mini that I pulled the 4GB HDD out of years ago and replaced with a 64GB SD card. I don't know why it is any different and all the iPod_Control files are sane and are not corrupt so something changed in the AMPDeviceDiscoveryAgent or AMPLibraryAgent, Finder, or whatever does the communications. Other than that, battery is good, SD card passes block-level fsck, and using as a storage device has zero issues.

Why do I use a 20 year old iPod? For starters, the interface / UI is far more intuitive and easy to use than the phone. It fits perfectly in my hand versus the iPhone. I can skip, pause, change volume in my pocket without having to look at it (and fall into a pothole or walk into traffic). Wired headphones don't need charging and don't cut out when in high traffic areas like a train station and several dozen bluetooth devices are competing for bandwidth. And yes, I've replaced the battery 3 times over the years :-)

How can I get to the dialog box asking permission to restore the iPod? All I get is "Connection Failed - Make sure "Macbook Air is turned on and in range." It is turned on and in range. I am BEYOND frustrated with this. I had my iPOD NANO 7 stolen. I have replaced it with a new one and now all it is is a brick that won't connect to my Mac. $%^&*&^%

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 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

También a mi me esta pasando no puedo sincronizar mi iPod nano o classic, como lo hacia de costumbre antes de la actualización a sequoia 15.5, tuve que acudir a un pc con Windows para resolver un problema. Que indignación tener que acudir a un PC WINDOWS para resolver un problema que ha generado Apple en su última actualización, necesito saber que tengo que hacer para volver a sincronizar mi iPod con mi Mac.

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.

I am an Ipod Classic user also wanting to sync his ipod to a macbook pro running Sequoia. Currently I am unable to do so.

Should I submit a bug report as well? Let me know.