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OP:

If nothing else works, you could try the free "Retroactive" app to make iTunes run on Sonoma.

Get it here:
(download the zip file)

It's been discontinued by the author with the release of Sequoia, but I know for a fact it will still work for iTunes in Sonoma.

Again, just something to try if you find that the "Music" app isn't working out.
Hi, this Retroactive app is ok, or 'itunes' but it likes to crash every time - now and then.... you found this??? i keep having to restart it.. sloely getting music on there.
 
What version of iTunes did you install?
Try 12.8.3.1, here is another method of installing iTunes on Sonoma https://forums.macrumors.com/threads/itunes-12-6-5-3-on-apple-silicon.2354390/

And install the latest packages required to connect iOS devices:MobileDeviceOnDemand.pkg & CoreTypes.pkg


Reboot after installing them.
 
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WTF all are you doing in this thread.

All they had to do was to open a Finder window and select the iPod in the sidebar like BigBlur said.
 
Right, looks like I found a way.... @Fishrrman suggesyion on reactive it worked - I think, got 2 tunes on there now... phew!!!!!
Goinfg to load more on now..
Sorry I am still i 2012 when it comes to apple..
They are way too overcomplicated.. They try too hard to be innovative when it really just starts to add too many layers to what should be simple...
If I go to the supermarket and I want to buy bread.... I just put it in my basket and pay.... If I had to explain it in Apple terms, I would need to pick it up and change baskets 5 times before I got to the checkout.
Anyway, time to load up my 8GB ipod!

Sorry, I hope I wasn’t too harsh to you. I of course hope you were able to resolve your problem completely and get your iPod all the tunes you wanted on it.
 
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Sorry, I hope I wasn’t too harsh to you. I of course hope you were able to resolve your problem completely and get your iPod all the tunes you wanted on it.
80%... Success as I was playing jazz in my shop today :)
 
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Isn’t iTunes discontinued? That’s old software. I had the 1st generation iPod with FireWire that’s a long time ago. Apple 🍎 music is way better than iTunes.
 
WTF all are you doing in this thread.

All they had to do was to open a Finder window and select the iPod in the sidebar like BigBlur said.
I have no way to add anything like this, not even any options.
 
I've come to the conclusion that even Retroactive can't work reliably with iTunes on Sequoia.

Since Apple's "Music" app has no free streaming radio tuner as did iTunes (with the ability to present "a list" of different stations from which to choose), it's of no use to me. At all.

Time to look for "other approaches".
I find that "Radiola" works well enough. But you need to know the name of the station to which you're trying to connect...
 
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