Has anyone found any solution to this? I've been wanting to do this for a couple of months now before I reformat my iPod library to put in a bunch of new songs.

I get a similar issue with my iPod classic, but iTunes is not in consideration here. What happens is that whenever I connect my iPod to MM4 on Win10, MM can see all the music, but disconnecting in *any* way makes the iPod not able to see said music. However, when I connect my iPod to my laptop with ...

Lowlander wrote:ALAC is a type of encoding, not the extension. You want to make sure that the AAC family of extensions is selected.

AAC was/is selected.

Peke wrote:MM 4.1.14+ support ALAC.

Can you upload one of files and send me DL link on PM in order so that I can analyze?

Sent.

Start here: http://www.mediamonkey.com/support/index.php?/Knowledgebase/Article/View/97/0/playing-m4a-m4p-m4b-aac-tracks Make sure the appropriate File Type(s) are enabled under File Types in the File > Add/Rescan Files dialog. Then use the Entire Library > Location node (enable under File > Manage...