Itunes / Iphone playlist problem

[ramonesfreak]

been using itunes forever. I hate it. It sucks so please no need to tell me. After building and maintaining this digital library of well over 100K songs, I finally quit using it because of the headaches

But, I got a new car and it has wireless apple car play and I have an iphone, so here I am.

The problem is this:

I make a play list using itunes on my computer (windows 10).

I sync the phone (iphone Xs running 14.4.2) and the playlist appears on my phone

BUT- lets say the play list has 40 songs on it (as I am looking at it on my computer) but when I look at the playlist on my phone, there is 1 song in the play list

This has only happened with music I purchased from itunes. Yes, I have the "show apple music" toggle set to on.

If I add the music to the play list while only using the phone (not involving computer at all), it will show up in the play list UNTIL I sync the phone again and I am right back to the problem

I have spent the last 3 hours googling and cant find this issue addressed other than the usual, turn on show apple music, etc...

The really odd thing is, when I have the phone connected to the computer and i am looking at the contents of the phone via itunes...the playlists are there and fully populated, but in reality (looking at the phone) they are not

The very odd thing that has me really stumped is, the 1 song that remains is also a song i purchased off itunes so the idea that this has something solely to do with purchased songs is not clear

[astrochex]

I would blame it on Windoze. That’s all I’ve got.

[GH85Carrera]

Blame it on iTunes. It is THE worst POS piece of software ever. It is worthless. I use it only to back up my phone to my computer.