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Jayson A

macrumors 68030
Original poster
Sep 16, 2014
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Ever since iOS 8 came out, I've had nothing but problems with syncing my iTunes music with my iPhone. You would think everything would just work together like they're supposed to, but sadly, that ended with iOS 8. Syncing music was flawless in iOS 7.

Here's why I'm so pissed:

1. Downloaded some music from iTune Store on my iPhone. They appeared in my "Purchased" playlist as normal (although sometimes not all of the songs will be added to "Purchased", but that's another problem all together). So, my purchased songs downloaded and played perfectly fine, all is well.... until I tried syncing with my computer (Mac by the way).

2. Plugged my iPhone into my Mac and start to sync. iTunes starts automatically downloading the songs I bought from iTunes (which is fine), but as my iPhone is syncing, it starts transferring the new music from my iPhone to my computer (meanwhile my computer is still trying to download them from the internet). So now I have duplicates of half of the songs. Ugh.

3. So, I look on my phone in the "Purchased" playlist and notice that half of the songs are now MISSING from that playlist, but they're still in my music library.

4. So I decide to delete the duplicate songs and re-sync. However, after deleting the duplicate songs, BOTH copies of the songs also get deleted at the same time!

5. Feeling pretty upset now, I decide to delete all of my recently purchased songs (13 of them) and just re-download them again. The downloads finish, so I try to sync again. Only this time, the "Purchased" playlist on my iPhone still doesn't show all 13 songs even though the playlist on the computer does. Ugh.

6. Finally, I went into my iPhone's music and manually deleted all 13 songs by doing "Remove Downloads" on each one and sync'd one last time. However, this time iTunes was stuck on "Waiting for sync to start", so I canceled it after some time... except it wouldn't cancel so I unplugged my iPhone (which didn't have the syncing symbol on it anyway, so nothing was actually happening).

7. So then I plugged my iPhone back in and clicked sync once again in iTunes. FINALLY, all 13 songs sync to my iPhone and it FINALLY looks exactly like it did before I tried to sync.

I like the fact that I can purchase music from my iPhone, but it shouldn't remove them from my playlist when I try to sync to the computer. The crappy part also is... this isn't just a one off incident. This crap happens to me ALL THE TIME when I try to purchase music on my phone and then sync to the computer. Most of the time the purchases are already finished downloading on the computer before I sync and they still get removed. It's almost like no matter which playlists I transfer them to, they don't show up on my iPhone in those playlists (but, they're still in my main library).

I almost ALWAYS have to manually delete the downloads from my iPhone and re-sync to get them to appear in the playlists. It's also weird that SOME songs sync and others don't.

Does this happen to anyone else? I've restored my iPhone's from scratch and set up as new and this crap still happens. I'm on the latest iOS 9.3 beta right now (but this isn't a 9.3 issue because it's been happening since 8.0).

I think it's because I refuse to use the cloud. I only show local music on my computer and my iPhone. Like I said earlier, iOS 7 always synced perfectly with my iPhone 5s, but right when iOS 8 came out, all hell broke loose and I have to do all these funky work-arounds to get it to work correctly. I don't know how many people use their iPhone for music as much as I do, but I am very organized and my library is very clean with album art on everything and tagged just right.

Sorry about the long post, but I was so pissed that I had to vent a little bit. Is it just me with this issue? Why can't it work like it's supposed to?
 
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Couldn't you disable automatic downloads for music in iTunes for the Mac and/or iPhone and stop it drop giving you duplicates?

I've never ran into the issues you're having. So I'm just taking a guess at something that might help.
 
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I disabled automatic downloads/sync but have had so much issues with sync in the past between iTunes (desktop) and my iPhone with both music and apps that I decided never to plug my iPhone in my desktop or use iTunes because of that. I use third party cloud music apps (CloudBeats Pro) to listen on/offline to my music just by simply dragging/dropping my music (mp3) in a folder and listen to it on my iDevices.
 
iTunes is horrible. No one will admit it.

I miss my Blackberry Pearl - better music player, easy drag and drop of music.
 
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Okay, so I bought some new songs today on my iPhone and I took Lagwgon's suggestion of turning off auto downloads in iTunes on the Mac. However, when I synced my iPhone, the purchases transferred, but removed themselves from the "Purchased" playlist. So therefore, that's how my iPhone synced.

So once again, I deleted the songs from my iPhone, moved them to the Purchased playlist on my computer and re-synced and that worked.

Seriously, this never happened before iOS 8 and like I've said before, this phone was set up as NEW and not from a backup.
 
iTunes can be a right pain in the proverbial, it needs to be torn down and rewritten from the ground up.

I'm dealing with support right now for a problem like you have in step one, a TV series not showing in my purchased list. Therefore I can't watch it on my Apple TV. I went through three levels of support and it has now been sent off to Cupertino.
 
iTunes can be a right pain in the proverbial, it needs to be torn down and rewritten from the ground up.

I'm dealing with support right now for a problem like you have in step one, a TV series not showing in my purchased list. Therefore I can't watch it on my Apple TV. I went through three levels of support and it has now been sent off to Cupertino.

I mentioned in a couple posts up. That Eddie Cue and Craig Federighi mentioning that iTunes on the Mac is getting a "refresh" next month along side the release of the 10.11.4 update.

So, it sounds like they might be making some efforts soon here to change iTunes.
 
I mentioned in a couple posts up. That Eddie Cue and Craig Federighi mentioning that iTunes on the Mac is getting a "refresh" next month along side the release of the 10.11.4 update.

So, it sounds like they might be making some efforts soon here to change iTunes.

Yeah, I saw that and I hope so. But I would be worried a 'refresh' is a lick of paint rather than a redo from scratch. I think the mess is because it's morphed into a huge behemoth of code from much humbler beginnings.
 
iTunes work fine for me; I only purchase from iTunes on the Mac. Not everyone hates iTunes.

Exactly! iTunes works just fine for me on the Mac. I only make my purchases there and then sync my iDevices. I even had Apple Music for a while without issues but got rid of it before I had to pay for it.

I wonder if the issue is with Purchased being a smart playlist? Try making a regular playlist and see if the problem persists there.
 
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