Q: Near Duplicate Playlist is Created when Syncing with IPhone

I installed iOS9 yesterday and it seems to have fixed the problem!

I wish I could say the same!

I've just installed iOS9 and now iTunes doesn't recognize my iPhone at all!

Why does like have to be so frigging complicated?

Apologies, I take my last comment back.

When I updated iTunes, I thought there was something fishy about the install.

Having uninstalled and reinstalled it, the playlist thing does seem to be solved with iOS9

However, I still have this weird thing with new purchases not showing up in playlists..

Does anyone else have this issue?

I have the same problem. I can see that the songs are meant to be there when I look at my iPod in iTunes, but they're not making it onto my iPod -for the last two weeks. Also, I created a new playlist last week, and though it's there in iTunes under my iTunes playlists and iPod playlists, it's never made it onto my iPod.

So frustrating!

Sorry to hear that.

All is fine with my iPhone 6, since the update to iOS9.

However, my old iPod Classic has had issues for sometime now

Sometimes it syncs immediately, others, it takes 4, or more connections for it to be recognized!

I keep trying! It's only been since I did the ios9 update that I've had problems. Perfectly OK until then!

I can confirm this is happening to me on iOS 9.0.2 with an OS X 10.11 host as well. Which means this is not a iTunes on Windows issue, but either an iOS issue or some flaw in the synching mechanism or iTunes code that is common to the Mac and Windows. It's basically made iTunes syncing so bad for me that I just listen to streaming radio on my iPhone now, as maintaining playlists is futile and more work than it's worth.

I have all of the afformentioned issues with syncing, but I have another two, which are TRULY annoying and really unacceptable as a user to have to deal with, does anyone else have these two issues:

1) EVERYTIME I sync now after iOS9, all of my album art dissappears and has to be re-synced, this happens EVERY time now, and I have 5000 songs on there

2) Sometime the sync fails, although it manages to create duplicate playlists in the process. the worst thing, is the iphone sometimes deletes playlist information in Itunes!!. Its one thing to mess up playlist information on the phone, but to mess up a playlist on your computer, is mind boggling, the sync causes duplicate playlists in both iphone and itunes. I can live with playlists being messed up on the phone, but NOT in my computer!

After it did that a few times, I started having to backup any playlist that was being modified before the sync by exporting the playlist.

It would be good if you had the option to make the sync either a two way sync (as it is) or turn that off and just have a one way sync from iTunes to iphone, that would alleviate a lot of these sync issues as the phone would be forced to just accept the new changes and not try to change itunes.

Same problem here, iPhone 4s just updated to iOS 9.2 and now i constantly get extra playlists when syncing.
Could have happened before the update too, don't really now as i stopped syncing a while ago due to another issue: iTunes keeps on creating duplicate (or tripple or even more) copies of my music files, not just in the library but actual duplicate files on the HDD taking up space.

Edit: Now my iPhone is full with music i didn't even sync there, but a new playlist that i actually wanted to sync onto it, ain't on there, but all the duplicate playlists still made it. Also my iPhone is complaining about a lack of free space, while iTunes shows it having still around 8 GB free space. What the **** is going on?

The only work around I've figured out is to connect your iphone to your computer.  In itunes, click on the iphone icon.   At the bottom under OPTIONS, click on Manually Manage Music and Videos (so it has the check mark).   In the left hand column, you can now delete any playlists on your phone by right clicking the playlist and choosing delete.

Prior to activating the Manage Music, I was adding songs to a current playlist in itunes.   When I went to sync, the songs wouldn't be added to the playlist on the phone, and also the songs I added would sometimes get deleted off my computers playlist.   Now if I add/subtract songs to a playlist in itunes, I delete that playlist off the phone, and then drag the good playlist from itunes into my phone.   It's been working well enough until Apple hopefully fixes the sync issues and all the other Music issues.

EDIT:  I should add that after you delete a playlist on the iphone while in itunes, itunes goes through Updating Files on "iphone" (kind of like a sync).   When it's done, you can then drag the playlist up from itunes into the iphone.   Make sure you drag it high enough so that you see the blue box appear and then drop it in the blue box.  Itunes will then again go though the Updating Files on "iphone" for a little bit.   When it's done, you're good to go.

If you lose your artwork after all of this, which sometimes happens (why I don't f'n know), then run a sync and the artwork should come back.

Just hopping on to say I've got the same problems as everyone else, same description, same fixes tried. Come on Apple. This is beyond stupid.

iPhone 4S, iOS 9.02

I Think I found the solution. if you ever created a playlist on your phone that is the problem. What I did I removed all my music from my phone and deleted the playlist I created from my phone. Then synced my phone with no music. Then turned off and back on. Then I put all my music back on and it worked

First off... Disregard everything I stated above.  It worked for a very short while, then went total FUBAR.  Apple has this so f'd up, that Jobs is rolling in his grave.  I never made a playlist off my phone until recently, since apple f'd this all up.   At this point, the ONLY way I can make a playlist is off my phone.  I will not sync ever again until apple fixes this problem.

I am having the same issue, just letting everyone know. I go into full rant mode in another thread, but one of the more helpful people on this forum (turingtest2) responded to the OP in the other thread, so that's why I responded fully to that thread instead of this one. His solution didn't work for me, though. :/ Feel free to chime in here:

ITunes creating duplicate playlists when syncing with iPod