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iTunes 8.1 breaks syncing with 2nd gen iPod shuffle

So, I downloaded iTunes 8.1 as soon as it came out as all the new features seemed pretty benign, and I've never had issues with any iTunes update going all the way back to 1.0. However, the 8.1 update rendered my 2nd gen shuffle no better than a $5 MP3 player.

Keeping in mind I use my shuffle primarily for listening to podcasts, here's the issues:

+1) dragging files to the iPod that already exist on the device+

8.0: pops a dialog warning that some of the items are already on the device and gives you the option to skip those ones and copy the rest. I use this all the time as I just do a select all and drag everything in my Podcasts list to the iPod to get new stuff onto it
8.1: it gladly copies the duplicates onto the iPod again

+2) order of podcasts when added to the iPod+

8.0: podcasts get put at the end but when you disconnect, they get moved to the beginning of the play order on the shuffle and are arranged in the same order as the sort set on your Podcasts list (in my case, ascending Date Released). This was great as all the podcasts would end up right at the beginning of the shuffle in the order I wanted
8.1: podcasts get put at the end and stay there, in whatever order they were in from the location I dragged them from (i.e. the literal order they appear in the Podcasts list. So while in 8.0 they'd be arranged in date order regardless of whether different podcast subscriptions were mixed together, in 8.1 they were placed into alphabetical podcast order, subsorted by date)

+3) automatic removal of deleted podcasts+

8.0: a podcast deleted from the Podcasts list that's also on the shuffle will immediately cause a sync event and remove it from the shuffle
8.1: no sync event, deleted podcast stays on the shuffle until manually removed

+4) ability to play songs from the shuffle in iTunes when the shuffle is connected+

8.0: double-clicking a song that's on the shuffle by selecting the device and then its Music tab, plays it (and also causes immediate and constant syncing, which is weird, but also expected)
8.1: double-clicking a song has no effect. Selecting a song and clicking iTunes' play button does nothing

The problems are occurring on my Mac Pro. I initially upgraded to iTunes 8.1 via Software Update, but tried reinstalling via the standalone installer. No luck. I also tried restoring the iPod to factory settings twice with no luck.

I also did some tests on my MacBook Pro which still had iTunes 8.0 on it. The same "correct" behaviour was encountered on the MBP. As soon as I upgraded to 8.1 via the downloaded installer, the same "incorrect/broken" behaviour was encountered as on the Mac Pro. I restored the iPod in iTunes 8.0 and 8.1 and that still didn't fix the behaviour when using it under 8.1. Additionally, on the MacBook Pro I removed the iTunes library and started with a fresh one just in case there was something funky with it.

Anyone else having these problems? I know at least one person whose 2nd gen shuffle works with 8.1 as it always had, so I'm not sure what's up with my shuffle.

Mac Pro 8 x 3.0GHz, Mac OS X (10.5.6), 6GB, 2.25TB, 2 x 24" Dell 2407WFP-HC

Posted on Mar 13, 2009 6:28 AM

73 replies

bcw99

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Mar 20, 2009 7:04 PM in response to KepiSW

I have the old 1 G shuffle (2nd gen) and have all the problems you list. What particularly ammused me was that after loading duplicate files without warning me, I noticed that itunes had managed to stuff "1.38 GB" onto my 964 MB shuffle. Man, that's messed up!

Mar 20, 2009 7:07 PM in response to bcw99

{quote:title=bcw99 wrote:}… I noticed that itunes had managed to stuff "1.38 GB" onto my 964 MB shuffle. Man, that's messed up!{quote}

Wow! I didn't know Apple could do a hardware upgrade by installing software. Those guys are geniuses! 😉

bcw99

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Mar 20, 2009 7:17 PM in response to Tom Sheppard

Yeah, you'd think that Apple would have hyped itunes 8.1's ability to violate the laws of physics. That's a real innovation.

DennisMK

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Mar 21, 2009 8:09 PM in response to bcw99

I'm pretty sure that iTunes only puts each file on the iPod once, but keeps track of where the multiple occurrences in the list are. The "1.38 GB" is probably how much space would be needed if it had put multiple copies of those files.

My biggest problem is that it only seems to play the files in the order that they were put on the Shuffle no matter how you order them in the list. But then if it played the first 40 songs/podcasts, it shows the first 40 items in the list as played when you sync, even if the files that were actually played are farther down on the list somewhere.

dkwillow

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Mar 22, 2009 7:14 AM in response to Joe Canadian

I use my 2g shuffle for podcasts and I had the same problem. The only way I could fix it was to "downgrade" back to 8.0.2.20. To do that you have to delete your itunes library file (itunes library.itl) and then reinstall the older version. You can find the older version by googling the version number. Once it was reinstalled, I had to chose 'add folder to library' and point it to my old itunes music folder. It found all of my podcasts and put them into the library. You then have to click the subscribe button beside all of the podcasts and you should be good to go again. You will lose all of your play counts and playback positions of the podcasts that you have. I don't purchase music on itunes, so I don't know if it screws up any of your purchased stuff to do this but you might want to look around on the forums about that issue.

Mar 22, 2009 8:34 AM in response to dkwillow

I documented the procedure I used here:
http://AppleNag.com/2009/03/12/itunes-rollback-nightmare/

It's not that bad. I just started out the wrong way but eventually figured out how to use the backups iTunes provides when it makes an incompatible change.

Mar 22, 2009 8:50 AM in response to Magnus Lewan

@Magnus Lewan I don't think that the people who designed the 2nd Gen Shuffle are to blame here. I think it's the asshats that designed the new 3rd Gen Shuffle mucking it up. Putting all the controls on the headphones? What a way to screw your customers over...or at least make them want to buy the next product up.

Mar 23, 2009 4:28 PM in response to KepiSW

Thanks for this. I am having all these issues as well with my 2G. After having a nightmare with my 1G shuffle I thought Apple wouldn't muck it up again.

Apple - if you are listening - this is not good enough. I expect poorly designed, developed and tested from other vendors but not from you. I pay a premium price for a premium product.

Mar 26, 2009 12:28 PM in response to DennisMK

I am having these EXACT same issues. I wish they'd do something to fix this. I'm tempted to ask them for a refund on my Shuffle since this update "broke" it. Has anyone heard anything from Apple regarding a fix???

VERY ANGRY about this mess!!!

Mar 27, 2009 4:36 PM in response to DennisMK

I have most of these problems with my first gen. shuffle.
I just wanted to add that deleting songs takes now a much longer time.
Sometimes deleting songs from the shuffle does not mean the memory
is freed. When I tried adding a song it replied "not enough space available",
which means that even adding items did not trigger the real deletion of the
old songs: in fact I detached the iPod, reconnected it and the old (deleted)
songs appeared again. I had to repeat the delete operation twice before
it had success.

Plynke

Level 1

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Apr 3, 2009 11:55 AM in response to KepiSW

Has anyone received any feedback from Apple yet? If you call in, do they replace it with a newer model? (They replaced mine with the same model and it broke too, of course)

<Edited by Moderator>

Apr 3, 2009 11:58 AM in response to Plynke

Apple is not known to provide any feedback. Either they fix it or they don't. In this case, your hardware is likely working correctly, especially if it was working in 8.0 but failed in 8.1. This is an iTunes problem.

Note that even with 8.0 there were still problems with the Shuffle, such as specifying the play order of podcasts, but at least it was tolerable. iTunes 8.1 is a non-starter for me.

DennisMK

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Apr 6, 2009 12:56 AM in response to KepiSW

I have found a workaround that seems to have solved all of my syncing problems so far.

While iTunes will let you move songs around in the list (when sorting by the left-most "item #" column), the Shuffle will only see the list by the order the songs/podcasts were copied to it. This includes, for example, syncing after listening to podcasts to remove the old ones and add new ones. I listen to podcasts primarily and use music to fill any "extra" space in case I finish with the podcasts before the battery dies. I really liked the way 8.0 automatically put the podcasts first and in order by date released from oldest to newest. Since 8.1 doesn't do that automatically, I need to do it manually. But simply removing the old podcasts and adding the new ones in the proper position in the list won't work. The Shuffle, when set to play straight through (not shuffling), will only play them in the order they were added. So the new podcasts will come after the music. And playing the music after any old podcasts that are still there will mark the new podcasts that were inserted above the music as having been played and not mark the music as having played. If you play in shuffle mode, it's anybody's guess what will be marked as played when you reconnect to the computer.

My workaround is to create a playlist to duplicate the Shuffle. Put all the files you want to sync into this playlist in the order you want them to be. Then select all of the items on the Shuffle and delete them. The select all of the items in the playlist and drag them to the Shuffle. Now the Shuffle sees the list in the same order you want it to. Playing straight through will play files in the order you set. Playing in shuffle mode will mark as played only those files that have actually been played. It's a bit of a nuisance having to do a couple of extra steps, and it takes longer since you have to re-sync files that were already there but had to be removed, but at least it works!

Apr 6, 2009 2:35 PM in response to DennisMK

oh my god it is so frustrating! it messes up the order, creates duplicates, doesn't record play counts, does anyone know how to fix this mess?!

thanks

Jason L

Community Specialist

Apr 6, 2009 2:55 PM in response to mikeoliver2106

Hey,

Try installing iTunes version 8.1.1.
You can download it here: http://www.apple.com/itunes/download/ or run software update as shown in the articles below.

If you have a Mac, this article: http://support.apple.com/kb/HT1338 will walk you through updating the Apple software.
If you have a PC, this article: http://support.apple.com/kb/HT2305 will walk you through updating the Apple software.

-Jason

iTunes 8.1 breaks syncing with 2nd gen iPod shuffle