iTunes support for 30-pin iPods?

Wow... I took the balky 2nd gen nano and connected it to the MacBook and just deleted about half the music on it. leaving about 1 GB free space. Then I disconnected it, plugged it back into the MBP (iTunes was not running). Et voila, iTunes 12.9.9.5 launched, the nano appeared on the desktop and in the iTunes panel and let me modify its content.

So it was about storage after all, not the capacity of that particular nano, but the too little free space. Been a long time since I even thought about free space on an iPod since once the larger ones came out I never even approached total capacity in usage. Learn something every day... now I know I need to overhaul what's on the rest of some of my older iPods that currently still do work with iTunes and latest operating systems, so I don't inadvertently run into that problem.

Thanks for your suggestion but there appears to be something more software-oriented in play here with respect to the 2nd gen nano, and in fact specifically with reference to that generation of nanos, since iTunes 12.9.x still "plays nice" with some other ones, e.g., 6th and 7th gen.

A little while ago today I thought to try the 2nd gen nano in question with a spare machine, my mid-2010 MacBook running El Capitan 10.11.6 and iTunes 12.8.2.3.

I have the 2nd gen nano's preferences set to open iTunes when I connect and also set to manage music manually. So I booted the 2010 MacBook and when I connected the 2nd gen nano, it was recognized immediately, triggered a launch of iTunes and mounted on the desktop with its nickname.

All that was what I would have expected it to do also on the MBP running Mojave and iTunes 12.9.x... But, the 2nd gen nano still won't connect to the MBP or at least is not recognized as doing such when I look at info from the USB tree in the system report for that machine.

Since I have not updated these nanos in a long time it's not clear to me from a successful connection to the 2010 MacBook this morning whether the problem on the MBP is related to iTunes 12.9 or to the Mojave OS on that newer machine.

Ugh... I guess I could sneaker-net a selection of music from the MBP over to the MacBook and then update the nano --and its companions, since I was thinking to refresh the contents of three or four of these 2nd gen nanos with different music when I first set out on this mission that turned into "a project" yesterday afternoon.

I don't regard this problem as solved. Not least because the 2nd gen nanos are still going strong, the MacBook is an older machine and my MBP although a mid-2012 model, was bought refurbed directly from Apple in 2016 and is still under AppleCare warranty so I'd expect that MBP model to remain at least my secondary machine into the 2020s since it's built like a tank.

All that said I realize the ipod nanos have been discontinued by Apple and carry assorted designations (supported, vintage, obsolete) which appear in practice not to be correlated in any particular way to how they work with iTunes.

Still I am mystified by any intentional removal of iTunes compatibility to something as relatively simple as a 2nd gen nano. Those little devices are practically indestructible too, so it's not like Apple should be surprised there are so many of them still in use!

And... as I said in my earlier post, my iPod Classic still connects to iTunes 12.9.x -- and so does my 6th gen nano, and my 7th gen nano. Both of the latter nanos get updated fairly often. These devices have more complex features than does the 2nd gen nano, so the disdain of iTunes 12.9 for the 2nd gen nano is quite puzzling.

Yah there's not going to be an update found: 1.1.3 is the last one available.

All my iPods were set up to enable disk mode. The feature is still shown on their summary panel although the option is greyed out now... but the box is still checked and the iPod nanos that do connect to iTunes do all also mount on the desktop with their nicknames and do allow the rudimentary data manipulation that was allowed on those devices, e.g. moving text files in and out of the device Notes folder, or just stashing stuff on them as if they were a USB stick.

The 2nd gen nano's model number I've been working with is MA477LL. It is a 2GB device. Its software version is already 1.1.3 and when it was connected to the MacBook, it responded to the request to update it by saying the software was up to date.

I have done more experimenting... and the plot thickens!?

Interestingly, two of my larger capacity (4GB) 2nd gen nanos (MA487LL) do get recognized and do let me modify the music / audiobook collections manually on the MBP running latest Mojave and latest iTunes 12.9.9.5. Those devices also of course run software version 1.1.3. No clue why a same-generation nano with higher storage would work and not the lower storage one.

That didn't really make sense at all, so next I picked a different 2nd gen iPod that has only 2GB storage and plugged that one into the MBP, and that one also does register on iTunes 12.9 under Mojave. But, the originally balky one still refuses to show up on that laptop even though it works fine on the 2010 MacBook running El Cap and iTunes 12.8.x

So now I'm almost out of ideas. Especially because the balky one does get treated like a valid iPod nano by the MacBook with the older OS and iTunes, and the other 2nd gen nanos all work there but also work on the MBP running Mojave and iTunes 12.9.9.5.

The only other possibility that occurs to me that could be related to storage issues is that the balky 2GB 2nd gen nano has only 255MB left of its 2GB nominal capacity. It's possible I guess that for some reason Mojave or iTunes 12.9.x requires a little more room to operate in. The other 2GB 2nd gen iPod I tried out, the one that works as well as the 4GB ones I tested, does happen to have relatively more free space left on it, somewhere around 755MB.

I think I'm going to restore the balky 2nd gen 2GB iPod nano to factory settings and give it another shot at connecting to the iTunes 12.9 under Mojave on the mid-2012 MBP. After that I'm going to put a sticky note on its back and say "use only with El Capitan" because I'm not rolling iTunes 12.9 back to 12.8 on the MBP just to find out if it's something related to how iTunes 12.8 and 12.9 operate differently under Mojave.

Thanks for your patience in trying to help me unravel this annoying little mystery. I'll report back if I can get the thing to work ok on the MBP with the current MacOS and iTunes.