iPod Classic no longer syncs with Ventura 13.2?

[Doc69]

I have just spent two full days and several calls to Apple support trying to figure out why my beloved iPod Classics suddenly stopped syncing with the Music app as well as iTunes (via Retroactive 2.0). After a lot of testing, it appears that everything works fine on 13.1 but not on 13.2. I would appreciate it if other people could confirm if it is the same for them or not. I have tried 5.5G, 6G, and 7G iPods, and it's all the same.

 

[eugenios]

Hi there,
I confirm the issue.
With iPod "sleeping" (screen off), if a sync is activated, iTunes pops out an error message (unknown error -25170), which I could also find in the log.
In this situation the iPod could be synced by closing iTunes and reopening it.
Once it has finished with the "pairing" with the iPod and the iPod screen is still on it can be synced without errors.

The strange is that (in my iMac) after rebooting (which by the way with 13.2 rebooting very often it ends with a KP) the iTunes <-> iPod classic sync is performing regularly.

I don't know what to say.
It looks like they fix a couple of bugs by breaking something that always worked before.

 

[Doc69]

In this situation the iPod could be synced by closing iTunes and reopening it.
Once it has finished with the "pairing" with the iPod and the iPod screen is still on it can be synced without errors.

The strange is that (in my iMac) after rebooting (which by the way with 13.2 rebooting very often it ends with a KP) the iTunes <-> iPod classic sync is performing regularly.

Just to clarify, you CAN sync your iPod classic on 13.2 if you reboot iTunes? When I connect my iPods to 13.2, they instantly go into 'Don't disconnect' mode, as they should, but then after a few seconds, they get out of this mode and are back to the normal main menu. But the iPod still looks like it's connected to iTunes (or the Finder), but when I try to sync, the iPod is actually not connected, hence the error message. So something in 13.2 makes the iPods disconnect a few seconds after they connect.

 

[pyramidic.shallot]

Just to clarify, you CAN sync your iPod classic on 13.2 if you reboot iTunes? When I connect my iPods to 13.2, they instantly go into 'Don't disconnect' mode, as they should, but then after a few seconds, they get out of this mode and are back to the normal main menu. But the iPod still looks like it's connected to iTunes (or the Finder), but when I try to sync, the iPod is actually not connected, hence the error message. So something in 13.2 makes the iPods disconnect a few seconds after they connect.

I have the same issue. I haven't found a way around it yet, no combination of rebooting Mac/iPod works - currently having to transfer my music to an old Mac mini and sync it that way. For other, older iPods, usually force quitting AMPDeviceDiscoveryAgent / AMPDevicesAgent / com.apple.amp.devicesui works, but no dice for the classic.

 

[Doc69]

As it seems like this is a bug, I would appreciate it if as many people as possible could send feedback about this issue to Apple. I just did and filed it under macOS. https://www.apple.com/feedback/macos.html

Here's what I wrote:

After upgrading from 13.1 to 13.2, I can no longer sync my iPod Classics with my music library in the Finder. But reverting back to 13.1 fixes the issue. And other people are having the same issue as well.

After connecting the iPod, it goes into 'Don't disconnect' mode, as it should, but after a few seconds, it disconnects and shows the main menu again. But in the Finder, it looks like the iPod is still connected, so when I try to sync, as the iPod is actually not connected, the sync fails.

The error messages I get are "The iPod cannot be synced. An unknown error occurred (-25170)" or "The settings were not saved for the iPod because it could not be found".

I would really appreciate it if this could be fixed since many people are still using their old beloved iPods.

 

[bogdanw]

Try to install the latest updates for CoreTypes.pkg & MobileDeviceOnDemand.pkg

https://swcdn.apple.com/content/downloads/49/27/032-06683-A_QRHIJ4BQOQ/jf8jwh5ejfbm5a11c2wqj2a6ahu6hb0qx1/CoreTypes.pkg
https://swcdn.apple.com/content/downloads/49/27/032-06683-A_QRHIJ4BQOQ/jf8jwh5ejfbm5a11c2wqj2a6ahu6hb0qx1/MobileDeviceOnDemand.pkg

 

[Doc69]

Try to install the latest updates for CoreTypes.pkg & MobileDeviceOnDemand.pkg

Wow, that actually worked! Even a senior advisor at Apple told me that 13.2 had removed this functionality! But I'm not surprised since the quality/knowledge of Apple advisors has gone down dramatically over the last few years. Anyway, I'm so happy that it worked and I can't thank you enough! I still use my old iPod classics daily so this was a huge disruption for me (a physical click-wheel is still superior to a touch screen in many situations). DM me a bitcoin address and I'll send you $100 as a token of appreciation. You really made my day!

 

[bogdanw]

Glad it worked.
"crypto" is a waste of energy

 

[Doc69]

Glad it worked.

Unfortunately, I spoke too soon. It worked the first time but not a second. The first time I connected the iPod after installing the files, the iPod display first showed 'Connected, then shortly after 'Synchronizing'. It was during this phase that I was able to complete an iTunes sync since the iPod was still connected. But the second time I started iTunes and connected the iPod, the iPod did not display 'Synchronizing', but instead ejected itself shortly after displaying 'Connected', just as before. So no sync was possible (same "An unknown error occurred (-25170)" message).

After some troubleshooting, I found that rebooting the computer and doing a hard reset on the iPod gives me one shot at a sync if I'm quick after I connect it (hitting Sync in iTunes while the iPod displays 'Synchronizing'). But after that, no more syncs are possible before rebooting both the Mac and the iPod.

Any more ideas?

 

[bogdanw]

Does Apple Configurator work with your iPod?
https://support.apple.com/apple-configurator
https://apps.apple.com/app/id1037126344

 

[Doc69]

Does Apple Configurator work with your iPod?

Unfortunately no, unless I'm doing something wrong. I assume it should mount automatically?

 

[LilySolutioMac]

I have just spent two full days and several calls to Apple support trying to figure out why my beloved iPod Classics suddenly stopped syncing with the Music app as well as iTunes (via Retroactive 2.0). After a lot of testing, it appears that everything works fine on 13.1 but not on 13.2. I would appreciate it if other people could confirm if it is the same for them or not. I have tried 5.5G, 6G, and 7G iPods, and it's all the same.

it maybe that the ipod is too old for such a new operating system i suggest an older version of macos? in. a virtual machine

 

[bogdanw]

Unfortunately no, unless I'm doing something wrong. I assume it should mount automatically?

I don't know.
Regarding iTunes, what version are you using? Did you give it Full Disk Access? If it already has it, try to remove the permission and add it again.

 

[stefaniecg]

As it seems like this is a bug, I would appreciate it if as many people as possible could send feedback about this issue to Apple. I just did and filed it under macOS. https://www.apple.com/feedback/macos.html

Here's what I wrote:

After upgrading from 13.1 to 13.2, I can no longer sync my iPod Classics with my music library in the Finder. But reverting back to 13.1 fixes the issue. And other people are having the same issue as well.

After connecting the iPod, it goes into 'Don't disconnect' mode, as it should, but after a few seconds, it disconnects and shows the main menu again. But in the Finder, it looks like the iPod is still connected, so when I try to sync, as the iPod is actually not connected, the sync fails.

The error messages I get are "The iPod cannot be synced. An unknown error occurred (-25170)" or "The settings were not saved for the iPod because it could not be found".

I would really appreciate it if this could be fixed since many people are still using their old beloved iPods.

@Doc69 Hi, i'm having the same problem.

If you downgrade to Ventura 13.1 you can syncronize your old ipods?

 

[Doc69]

If you downgrade to Ventura 13.1 you can syncronize your old ipods?

Yes. I installed 13.1 on another disk and copied my iTunes library files over before syncing. Then it works normally as before. But this obviously is not a great solution, having to boot into another OS just to sync. But at least it's there.

 

[Doc69]

it maybe that the ipod is too old for such a new operating system i suggest an older version of macos? in. a virtual machine

As the iPods work fine on 13.1, they shouldn't be too old. As for running iTunes in a VM, that works fine for small libraries. But since I have over 100K songs, over 100 playlists (many smart), and thousands of podcasts in my iTunes library, it's already super slow running natively on my Mac (last 6-core intel Mac mini with 32GB RAM), with long beach balls wait times when switching between Music and Podcasts, for example. So unfortunately the VM route is not an option for me.

 

[Doc69]

Regarding iTunes, what version are you using? Did you give it Full Disk Access?

I'm using iTunes 12.9.5, the latest version available via Retroactive 2.0. I gave iTunes Full Disk Access but no change (also toggled on and off). During testing, I reinstalled MobileDeviceOnDemand after a successful sync, and was able to sync again after two tries without rebooting. But I have not been able to reproduce this successfully again. After a first successful sync, which can only be made after a reboot of both iPod and Mac, the iPods always eject themselves shortly after connecting. Any more ideas?

 

[bogdanw]

I got a suspicion and half of an idea
My suspicion is that Finder is trying to take over the iPod, causing it to be disconnected from iTunes.
My idea would be to stop Finder doing that by terminating the related processes responsible, AMPDevicesAgent & AMPDeviceDiscoveryAgent, from Activity Monitor or from Terminal

killall AMPDevicesAgent; killall AMPDeviceDiscoveryAgent

 

[Doc69]

My idea would be to stop Finder doing that by terminating the related processes responsible, AMPDevicesAgent & AMPDeviceDiscoveryAgent, from Activity Monitor or from Terminal.

Only the AMPDeviceDiscoveryAgent was running for me. And after stopping it, the iPod no longer mounts in the Finder. But unfortunately, it didn't help. In fact, after several reboots and tests, all the podcasts disappeared from the iPod at some point and I'm also no longer able to sync it, even after a reboot of both Mac and iPod, as it now disconnects pretty immediately after connecting. Very buggy stuff, hard to find any logic here! So I had to copy the iTunes library files to another volume with 13.1, and sync ut there to bring everything back.

I also just remembered that I removed the "iTunes Helper" from loading automatically a while back. But this shouldn't be related, I think?

Any other ideas?

 

[bogdanw]

I also just remembered that I removed the "iTunes Helper" from loading automatically a while back. But this shouldn't be related, I think?

You can re-add it from /Applications/iTunes/iTunes.app/Contents/MacOS/iTunes.app/Contents/MacOS/iTunesHelper.app

 

[Doc69]

You can re-add it from /Applications/iTunes/iTunes.app/Contents/MacOS/iTunes.app/Contents/MacOS/iTunesHelper.app

Interestingly, iTunesHelper.app was not present in the 12.9.5 version of iTunes that Retroactive installed. But I found it in an old version on another drive. Didn't make a difference though.

Anyway, thank you for your help. I have spent countless hours troubleshooting this issue, and now it doesn't work, even if I reboot my Mac and the iPod (which is super weird since it worked consistently a few days ago). But at least I can copy the library files to another volume with 13.1, boot from it, and then sync there. If you have any more ideas, please let me know. Otherwise, hopefully, it will get fixed in 13.3.

 

[chadamorrill]

Sorry to report that I just plugged my 4th gen iPod to our M1 Mac Mini running 13.2.1, and it syncs with no issue at all. Ejecting is still a bit wonky, but I've learned to just be patient for that.

 

[eugenios]

Hi everyone,
after updating to macOS 13.2.1 iPod classic with iTunes 12.9.9.5 is now working as it was in macOS 13.1.

 

[Doc69]

Hi everyone,
after updating to macOS 13.2.1 iPod classic with iTunes 12.9.9.5 is now working as it was in macOS 13.1.

Same here. Finally, after the 13.2.1 update, my iPods are syncing normally again!

 

[Doc69]

Did anyone try iPod classic syncs in 13.3? Before I upgrade I would like to make sure this issue won't happen again.

UPDATE: I just tested 13.3 on another partition and it synced fine.