itunes: please dumb this down for me

[Mac'nCheese]

I know this should be simple and I've tried every thing I've searched for and it still won't work. Simply: I hooked my son's ipod shuffle up to my new imac. I want to delete some songs off of his ipod and then put some new ones I just bought (I see them in itunes) onto his pod. Nothing is working. Not dragging and dropping, not hitting delete, not using some of the pull down menus....all the things I read about in the itunes help and from google searches. Can anyone help me?

 

[Audit13]

Tried doing a complete reset on the shuffle via iTunes?

 

[HobeSoundDarryl]

I'm guessing you might be trying to drag songs onto the iPod icon?

Have you tried, copying the new songs into a playlist in iTunes, then synching that playlist to iPod? http://www.wikihow.com/Sync-an-iPod That's the most common way to get iTunes music onto an iPod.

 

[0002378]

Sorry you're having trouble. iTunes is, in my experience, one of the crappiest pieces of software ever written. Its behavior is the antithesis of user-friendly. I got so frustrated with it that I ended up writing my own mp3 player app.

Anyway, the only thing I can think of is this ...What you describe sounds like a genuine iTunes bug. You may want to try changing iTunes version, because bugs sometimes get fixed or introduced in different versions. If you're using the latest, try installing an older version. And if not, try upgrading to the latest version. Sometimes, this is the simplest and best salvation to be found.

 

[albusseverus]

I know this should be simple and I've tried every thing I've searched for and it still won't work. Simply: I hooked my son's ipod shuffle up to my new imac. I want to delete some songs off of his ipod and then put some new ones I just bought (I see them in itunes) onto his pod. Nothing is working. Not dragging and dropping, not hitting delete, not using some of the pull down menus....all the things I read about in the itunes help and from google searches. Can anyone help me?

Your description of the issue is a bit light-on. Are you talking Apple Music tracks? etc…
You have to do things the Apple way, when it comes to iTunes. Trying to be smarter than the system never ends well. I love iTunes, keeps my media library in one place, but Apple is slowly killing it and removing functionality.

iMazing may help if iTunes won't dance for you, not sure if it does shuffle, though. https://imazing.com

Try these references, see if it helps. Looks like Shuffle has dropped off their official syncing support doc, which doesn't look good.

https://support.apple.com/kb/PH19458?
http://appleinsider.com/articles/15...-shuffle-wont-sync-offline-apple-music-tracks
https://support.apple.com/ipod/ipod-shuffle

Best of luck.

 

[Mac'nCheese]

Thanks guys. I've been a little busy but when I get a minute, I'm going to go through all the advice at home and hopefully one of the tips will work.