It's been about half a year since I moved from an iPhone to a Windows Phone. This was a particularly difficult decision, as play counts are extremely important to me but non-Apple devices don't sync media play counts with iTunes. (More on this in a bit.)
But I switched anyway, and I bought a 4th-generation iPod shuffle as a replacement for the Music app on my iPhone as well as a cool little fashion accessory in my favorite color. I never listen to any music from my iTunes library on my Windows Phone; the only music-related thing I do with it is watch music videos on the Internet — I don't store any music videos on iTunes anyway.
In the six and a half years I'd been using an iPhone, play counts and other metadata synced perfectly with iTunes (well, except when it was completely fudged in iOS 8.0 until it was fixed several months later in iOS 8.1.1). Not so with my iPod shuffle; I've noticed that when I sync, sometimes the play counts, skip counts and last played/skipped dates update, and other times they don't even though I could have sworn I've been listening to my music all day.
What gives?
Best Answer
I didn't think of posting this question until today but after a few weeks of experimentation, I've determined that, for some strange reason, iPod shuffle will only update play metadata when, before my next sync, I either
If I don't finish listening to a playlist (which can be the case with very large playlists), the metadata will not be updated on iTunes.
Powering iPod shuffle off and on between listens does not appear to make a difference, but I'll report back with any new findings. For what it's worth, in normal use, these are the steps I take when preparing to sync:
And of course I always eject it from iTunes before disconnecting it.