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flaubert

macrumors 6502
Original poster
Jun 16, 2015
438
166
Portland, Oregon
Hi, so I'm trying to get used to MacOS Monterey (I know, late to the party). I have an iPod Nano 6th Gen, the small square one with a display that clips on your clothing. It connects via USB and a 30 pin connector cable. I am mystified about whether Monterey even supports this 2010-era device... I plug it in, and it shows up in the sidebar of Finder. Originally when I did that it showed me choices in the window to the right: General, Music, Podcasts, and maybe one other (Pictures?). I mostly use this iPod for podcasts; when I clicked on the podcasts link it changed the Finder window display to show an empty listing of podcasts. I think that there was button to choose podcasts, but when I clicked on it there were no podcasts to choose - this was true, even though opening the Podcasts app shows the podcasts that I'm following. I simply could not figure out any way to get podcasts transferred to the iPod - I couldn't drag them from the Podcast app, nothing. Right clicking in the empty list did nothing.

I read a posting in this section of the forum that suggested that you had to factory reset an iPod to get it to work properly under later versions of MacOS. So I dutifully clicked on the "Restore iPod" button in the Finder display. It downloaded 12 MB of an update, seemed to install, although the window said "updating iPod" for far longer than I thought it should take. I waited ten minutes, then clicked the other iPod entry in the sidebar that had an eject symbol. It ejected just fine. Now when I reconnect the USB cable the iPod still shows up, but there are no little tabs/links to do ANYTHING with it. All I get is the button to Check for Update and the button to Restore iPod.

When I open the Music app the iPod doesn't show up there, either. I can't be sure, but I think it did show up there prior to restoring the firmware.

So, it appears that I'm totally dead in the water as far as using this iPod Nano 6th gen device under Monterey. Any ideas?
 

Grumpus

macrumors regular
Jan 17, 2021
184
93
I have three old iPods, a 4th gen Photo, a 2nd gen Nano, and a 7th gen Nano. Monterey won't sync any of them properly. So, I used Retroactive to install iTunes 12.9.5 which works with them all. Retroactive can also install a couple of older iTunes versions, but I don't have any direct experience with those.

If you decide to go this route, there are a few things to be aware of. First, Apple doesn't provide a direct download of iTunes 12.9.5, so Retroactive downloads a copy of the Mojave installer and extracts iTunes from that. This is a large download and the process can take quite a while.

Next, you can still experience problems using iTunes to sync your iPod, stemming from the fact that the OS machinery used to support the new Finder-based scheme is still running. Specifically, AMPDeviceDiscoveryAgent can cause syncing to fail, or cause other strange sync-related problems such as already-listened-to podcasts being re-downloaded.

The solution for me is to kill AMPDeviceDiscoveryAgent. You can do this "by hand" by running the following command in a terminal:
Code:
/usr/bin/pkill -SIGTERM AMPDeviceDiscoveryAgent
That's not very convenient, even if I could always remember it, so I'm using a launch agent to do it. The directory ~/Library/LaunchAgents doesn't seem to exist by default on Monterey, so you may have to create it:
Code:
mkdir ~/Library/LaunchAgents
Then, save the following as ~/Library/LaunchAgents/local.AMPDevicesAgentMustDie.plist
Code:
<?xml version="1.0" encoding="UTF-8"?>
<!DOCTYPE plist PUBLIC "-//Apple//DTD PLIST 1.0//EN" "http://www.apple.com/DTDs/PropertyList-1.0.dtd">
<plist version="1.0">
    <dict>
        <key>Label</key>
        <string>local.AMPDevicesAgentMustDie</string>
        <key>Program</key>
        <string>/usr/bin/pkill</string>
        <key>ProgramArguments</key>
        <array>
            <string>pkill</string>
            <string>-SIGTERM</string>
            <string>AMPDeviceDiscoveryAgent</string>
        </array>
        <key>RunAtLoad</key>
        <true/>
    </dict>
</plist>

Now AMPDeviceDiscoveryAgent will be killed after you log on. This can take a minute or two.

This solution works well for me, but might not be completely satisfactory for everyone. iTunes may not be able to sync very new iPhones and killing AMPDeviceDiscoveryAgent prevents the Finder-based scheme from working. It may be possible to modify the script that Retroactive installs to issue a SIGSTOP to AMPDeviceDiscoveryAgent just before invoking the "real" iTunes, and then issue a SIGCONT when iTunes exits. This might give you the best of both worlds, but since I don't sync anything to my iPhone I haven't actually tried it.

I should mention that restoring an iPod from iTunes works, but iTunes will probably crash at the end of the process. Simply restart it with the iPod still plugged in, and you should be greeted by the "Welcome to your new iPod" screen.

All of the above assumes that you're using an Intel-based Mac - I have no idea if iTunes can run on any of the new M1 or M2 machines. I also don't know if the above works on Ventura, although I think it should.
 

flaubert

macrumors 6502
Original poster
Jun 16, 2015
438
166
Portland, Oregon
Oh, my gosh, @Grumpus that is an amazingly detailed and well-documented answer. Thank you, and wow. What you're confirming to me is that yes, Apple really could not care less about those of us with functioning but old hardware. It's not just a case of Apple hiding the interface bits (as they do so often), but rather it just doesn't work. I was thinking of converting my existing Mojave installation to a virtual machine for other compatibility reasons, but maybe syncing my iPod is another reason to add to the pile, assuming that I can figure out how to connect the physical iPod to the virtual USB port in VirtualBox.
 

Grumpus

macrumors regular
Jan 17, 2021
184
93
Attaching your iPod to a VBox VM is fairly straightforward. When you plug the iPod into the host, it will probably auto-mount. Eject it, but leave it plugged in. Then, with your VM running, in the menu bar select Devices -> USB -> iPod and it should be attached to the VM. After ejecting the iPod in the guest, do the reverse in the Devices menu, i.e. uncheck the iPod, before unplugging it from the host. Before you create the guest VM, don't overlook to install the VirtualBox Extension Pack, that's required for USB to work.

I'm still running VirtualBox 6.1.40, mostly on a Fedora host, but I've also done some testing on a mid-2010 MBP running High Sierra. I briefly tried the new 7 version, but soon reverted because of display issues. On 6.1.40, the Darwin version of guest additions fails to install, and from google I get the impression that's a universal problem. You lose a number of things without guest additions (drag-and-drop between host and guest, shared folders, shared clipboard) but otherwise things work ok, as long as you remember to install the Extension Pack.

Another possibility for you might be to install Mojave on a USB drive, booting from that whenever you want run iTunes. I considered doing that, but I mainly use this 2019 MBA with only 2 USB-C ports and fiddling with dongles gets old.

Have fun!
 

flaubert

macrumors 6502
Original poster
Jun 16, 2015
438
166
Portland, Oregon
OK, so this is weird, but worth reporting: I have a MacBook Air (2017) also running Monterey. I figured I had nothing to lose, so I plugged the same iPod Nano 6th gen into that laptop, and was given the option to load music and podcasts to the device! I don't know if my earlier failure with the Mac Pro 5,1 was some obscure artifact of running unsupported Monterey via OpenCore, or what. Anyway, I'm able to load and listen to podcasts now, so all's well that ends well.
 

MBAir2010

macrumors 603
May 30, 2018
5,644
5,354
open minded
my iPod 2016 syncs with MBA_M1 well:
I can try to give any advice eon how to sync, but min just "syanc'd'
Screenshot 2022-12-21 at 6.47.26 AM.png
 

Grumpus

macrumors regular
Jan 17, 2021
184
93
I haven't tried doing a Finder-based sync since Monterey 12.5, which would not work on my 2019 (Intel) MBA. Attempts to sync would return immediately, with no data being transferred to the iPod. I tried all 3 of my iPods with the same results. Attempts to Restore an iPod would just go off into the weeds, never completing, preventing the laptop from being rebooted saying that an operation on an IOS device was still in progress (these aren't IOS devices, but ok). After a forced shutdown, the iPod would be corrupted and I'd have to restore using iTunes on another computer.

I'm on 12.6.2 now and maybe things have been fixed. I'm curious, but not really curious enough :)
 
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theorist9

macrumors 68040
May 28, 2015
3,129
2,270
You may not like this solution, but it works well for me: I've kept my 2014 MacBook Pro (running High Sierra) in part so that I can continue to sync my iPods with new music and Audible audiobooks using a native installation of iTunes. It's really convenient to do that in iTunes since it handles both. [It never made sense to me that they put audiobooks into Books instead of Music, since functionally they're digital audio files, and thus handled much more like music.]

You could probably get a cheap Macbook Air from that era (2015 models are selling for ~$125 on eBAY), put High Sierra or Mojave on it, and dedicate it to syncing your iPods.

The downside is that, at some point, Audible and iTunes might stop working with High Sierra/Mojave (Mojave is the last OS that natively supported iTunes).

Or you coud get a later-model MacBook Air or MBP (but it would have to be made no later than Sept. 2019; after that, you won't be able to install Mojave).
 

SPJones

macrumors member
Sep 3, 2022
56
15
Just the thread I was looking for!

I want to give my kids a cheap music/podcast player, and the local second-hand store has iPod Nano (4th-6th gen) for a very fair price.

I'm running Catalina on a 2013 iMac (so separate Music/Podcast apps, no iTunes).

Would I be right in thinking the iPods would sync fairly well within that setup, or am I likely to run into problems?
 

SPJones

macrumors member
Sep 3, 2022
56
15
The iPod Nano 6th Generation is an older Apple device that was released several years ago. It's a compact media player with a touchscreen interface. On the other hand, "Monterey" refers to macOS Monterey, which is a version of Apple's macOS operating system.

Here's some information about both the iPod Nano 6th Gen and macOS Monterey:

iPod Nano 6th Generation: The iPod Nano 6th Gen was released by Apple in 2010. It's known for its small size and square shape, featuring a 1.54-inch color touchscreen. Some key features of the iPod Nano 6th Gen include:

  • Music and Video Playback: The iPod Nano 6th Gen supports music and video playback, making it a portable media player.
  • Touchscreen Interface: It introduced a touchscreen interface that allowed users to navigate through their music, videos, and settings.
  • Clip Design: The device had a clip on the back, making it easy to attach to clothing or accessories.
  • Fitness Features: It included fitness tracking features with a built-in pedometer and Nike+ integration.
  • Limited App Support: Unlike later iPod Touch models, the iPod Nano 6th Gen had limited app support and primarily focused on media playback.
🤣🤣
 

ThunderSkunk

macrumors 68040
Dec 31, 2007
3,699
3,841
Milwaukee Area
Short answer: No. Apple doesnt support their own hardware.

…Sure they became successful by making premium hardware from metal and glass to last decades, but you cant expect a small company like Apple to spend their limited resources actually supporting all the stuff they’ve sold you. They’d have to pull one of their 12 programmers off the next finicky convoluted method of controlling 2 of their computers together. And as MR expert shareholders will explain, hiring more programmers just results in less productivity, so this is really the best of all possible worlds. Wouldn't you rather just buy some exciting new things? Wouldn’t it be easier? If you want any of this “antique” (anything older than my attention span) software or hardware to continue to function, get an intel mac running windows on it, because for some reason Microsoft‘s backward and stupid business model is ultimately what keeps Apples hardware working after a few years. But be forwarned, your iPod won’t have the latest security updates, and could be taken over by Al Queda AT ANY TIME

#1 most infuriating thing about the apple bubble
 

Tonytonem

macrumors newbie
Sep 4, 2023
1
0
Wow! That was interesting, anyway I had the same problem as the original poster. I inherited a rare vehicle from the 80’s and a $400(80’s) head unit. It does not have Bluetooth or an auxiliary jack for an iPod, but it does have a Pioneer iPod adapter which plugs into the rear. Well, the connector at the end is a 30-pin male jack so it WAS A MUST to acquire an OLDER iPod device. I proceeded to plug it in to my MacBook Air(2017) Monterey w/ iTunes 12.9 and unlike the eventual solution that the OP obtained, it kept crashing on the restore. Sooo, I followed one the above suggestions and used Retroactive as I had done to originally obtain iTunes 12.9, but this time I installed 12.6 instead. Plugged the iPod 6th in and it immediately appeared in the leftmost iTunes column ready for business, NO restore needed. MacBook Air(2017), Monterey-iTunes 12.65 accepts older 30pin iPod… and who cares about major security breach’s and updates on an older iPod? It’s music and maybe a couple naked photo’s of an Ex. Enjoy your days everyone🥳
 
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