iPod iPod shuffle 4th Gen and new music

[qubex]

Hello.

I’ve treasured an iPod Shuffle (4th Gen, Gold, 2GB) for a special occasion… and the time has come.

I’m facing the following problem: I want to put three (3) songs onto this iPod, and I’ve created a special playlist containing them. One of them was ancient (actually, all three of them are of the “Golden Oldies” variety) but one was a very old MP3 or AAC file I downloaded from iTunes probably sometime in 2005, while the other two are of the “Apple Music” generation.

I know the streaming music service is incompatible with these “classic” era iPods so I went ahead and also “bought” the two songs from iTunes Music store, and added those to the playlist instead.

Unfortunately, I get error messages telling me that of the three songs, two (the newest acquisitions) do not sync.

Does anybody know how to overcome this? (Amongst the various hypotheses I’d be willing to entertain I’d be perfectly willing to “re-buy” the two tunes from another service and then importing them into iTunes, provided it’s a compatible format without any form of DRM that will thwart my ultimate goal).

I hope somebody here can help me get to the bottom of this.

Thanks.

 

[mannyvel]

Unfortunately, I get error messages telling me that of the three songs, two (the newest acquisitions) do not sync

Can you post the specific error message?

You an also try clicking on the songs in iTunes then going to File->Convert and see if you can choose "Create iPod or iPhone version." You could also try converting it to AAC from that menu too. I believe the converter will use whatever the AAC settings are in Preferences->General->Import settings. Then drag the song back into the playlist.

 

[Slix]

Make sure the songs are the correct formatted files by right clicking on the song and clicking "Song Info", then "File". They should be "Purchased AAC audio file" tracks if they were bought from iTunes. It's possible that even though you purchased it, the song in the playlist or in your iTunes library is still the Apple Music track.