iTunes not syncing all songs/playlists

Hello ianparish

I would check two things, one create an new file by right click and convert song. Then try to sync and see if it moves the newly created song go over. You can also enable manually mange music to drag and drop the songs you want to your iPhone.

Managing content manually on iPhone, iPad, and iPod

http://support.apple.com/kb/HT1535

iTunes: How to convert a song to a different file format

http://support.apple.com/kb/HT1550

Thanks for using Apple Support Communities.

Regards,

-Norm G.

I just encountered this problem a few days ago, and what worked for me was going under the 'more' section of the music library on my phone and selecting 'shared' then selecting 'my library'- hope this helps future people.

Wow, found your response by chance and cannot thank you enough. What a crazy fix to a very frustrating problem! Thanks again.

Many thanks, CooltrainerJeff. After much searching and attempting countless previous fruitless attempts to solve the problem of my playlists not synching, your solution appears to have worked.

Correction: that didn't actually sync the songs in my playlists.

I'm trying this now, and it will probably work. But let's not say this is a "fix", not when you have a large music library and it will take 2 complete resyncs to get things configured to where they should have been in the first place. It shouldn't happen in the first place!

I won't get into the insignificance of iOS, it's really the major step backward that iTunes 11 took. Not only does it have one of the worst, inconsistent interfaces that ignores where you were if you click away, but its management of iPods and iPhones have been plagued with problems such as this. I've given up on iTunes Match and will be discontinuing that service as well.

Apple needs to get back to testing this stuff and keeping the bar high. These issues are the reasons we all left other platforms and is doing Apple no favors, no matter how much gorilla glass and aluminum you thrown on it. We bought into Apple because it worked, something that is becoming more and more less true (can I please stop typing my Apple ID password for every free purchase?).

Oh and I saved this before posting. I've just finished trying the above, and it didn't work.