iTunes music syncing madness

So my wife bought a song on iTunes. I liked it, thought I’d download it too. On my iPhone I head to iTunes Store and grab it via its cloud icon in the Family Sharing section. It plays. Great. I add it to a couple playlists and sync the iPhone to my Mac. Done. Great.

A couple days later I realize on my Mac the song is nowhere to be found. Neither in the playlists, nor if I just go to the song lists and sort by date added.WTH? Turns out it is indeed nowhere on my Mac despite iTunes syncing doing its thing just fine.

In the end, I had to accept that my iPhone and my Mac were out of sync. Instead, on my Mac’s iTunes I had to go to the store, Family Sharing section and go grab the song through its cloud icon again. Then it would play on iTunes and I can add it to my various playlists again. Finally, I can then sync my iPhone again, and only now are iPhone and Mac in sync.

Seriously, Apple. AYFKMWTS???