iTunes Playlists Not Syncing Correctly...Again!

iOS and iPadOS

So, since the latest update to iTunes and the release of iOS 9.1, iTunes is, once again, not syncing my playlists correctly. I though they had this fixed in the previous version, but, lo and behold, syncing issues are back again.

BTW, I am syncing with an iPhone 5 and with a Windows PC.

After I purchase a new song from iTunes and try to add it to a playlist, then sync my iPhone, that new song will not show up in that playlist on my iPhone. Neither will it show up even in the Recently Added iPhone native "smart playlist". However, it will show up as being added to the phone if I search for it.

Strangely, ifI add songs previously ripped from CDs to playlist, they add just fine.

I haven't tried adding songs purchased from iTunes before this latest update.

In any case, can anyone help me out here?

Usually when I un-sync all my music and re-sync it again, that takes care of the problem, but only temporarily. The next time I try to purchase a new song and add it to a playlist, the same thing happens, so I have to un-sync/re-sync again.

Does anyone have a quicker and/or more permanent fix for this?

Has anyone else even had this issue? If so, has anyone reported it to Apple? If so, what has been their response?




Submitted by Chris Bruinenberg on Saturday, November 7, 2015

I am having the same exact issue, one thing I would suggest is to start your music library over. Yes I know, it's a pain. I think it's the only way to fix it though. Good luck

Submitted by Misty Dawn on Saturday, November 7, 2015

Um, no.

It's quicker to re-sync than do that.

Also, the issue actually seems pretty universal, from what I'm hearing.

I just wish Apple would get is s*** together when it comes to these syncing issues...