Apple Event: May 7th at 7 am PT

Looks like no one’s replied in a while. To start the conversation again, simply ask a new question.

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

Reply
73 replies

Jun 1, 2009 7:13 PM in response to KepiSW

Ok folks, a mix of good news and bad news when it comes to the just-released iTunes 8.2.

Referencing the problems I outlined in the first post of this thread, issues #1 and #3 have been fixed (yay!) while #2 and #4 remain. At least those two issues are less of an annoyance (especially #4).

So just to be clear: issues #1 and #3 are fixed in iTunes 8.2; the old "correct" behaviour of iTunes 8.0.2 has been restored for both issues.

Jun 3, 2009 4:55 PM in response to Magnus Lewan

I've noticed that when I try to drag too many podcasts to the list I'm warned that there is not enough space and only the ones that fit will be copied. That seems to work, although it would be nice if they told us how much more free space was needed.

So I switch to the Settings tab to find out how much free space there is, look at the remaining podcasts, do some mental arithmetic and try to calculate how many songs I have to remove. Delete them and go back to Settings to check on free space. *It's not updated.* It used to work, but it's broken now. Geez!

I really wish Apple would run proper regression tests whenever they "fix" things. These kind of bugs should not be leaking through design, let alone verification.

How about allowing a rule that says "remove tracks most recently played" or "remove oldest tracks" or something so that this process can be automated. Why should I have to fight to get content on the Shuffle? A warning is fine, just give me the option to automatically delete and complete the copy.

Jun 6, 2009 9:46 AM in response to schpydurx

Indeed, 98% of the focus in this thread seems to be about podcasts, but my issue has to do with re-ordering songs. I do plan to gradually try all the things I used to be able to do.

2 things, though. One it seems the manual sync command in the File menu has made a return, it was grayed out in 8.0 versions after it's initial release. If I move stuff around it does NOT "seem" to re9sync, so it gives me some peace of mind to do it manually.

Second, has anyone noticed they seem to have less space available? I have always done random autofill and have my Shuffle play "in order." Depending on large songs, I have always varied between 280 and close to 300 on my Shuffle. For some reason I can't seem to get more than 275 now. The overall size data seems to say the ~275 is correct, but I don't remember what it used to tell me about the overall time. For some odd reason, I'm speculating it stripped any embedded covers in the past, but doesn't now. That WOULD explain what I'm seeing, but I have no idea if I'm correct.

Jun 8, 2009 1:30 PM in response to Riverside_Guy

A little more extensive testing and I think my issues are solved.

However, it SEEMS it may partially be the return of the manual sync that has done it. When a shuffle is synced, we get a long message that "iPod sync is complete. Eject before disconnecting" in the main info window of iTunes. If I move around songs, I do NOT get even a quick flash of such a message (pre 8.0 versions did flash a shorter message when songs were moved). But I do get it when I do a manual sync.

Anyway, 8.2 for far seems to have the olds behavior back and for once, a bug affecting discontinued Pod has actually been fixed.

BTW, I found out what was up with many less songs... when I set the playlist that feeds stuff to my pod, I set it to not copy songs 8 minutes or longer. THAT made it add a LOT of 6+ and 7+ minutes songs, diminishing the overall number of songs. Once I eliminated that requirement, IU'm back to a more normal 287 songs.

Jun 29, 2009 3:16 PM in response to KepiSW

I have come across a new development in the 2nd gen iPod Shuffle sync issue. My LSR iMac running Tiger (pictured at left) refused to power up after a power failure. It looks like either the power supply or the logic board may have been fried. I haven't been able to determine which yet. But for now, I'm using a white 13" Intel MacBook running Leopard and everything is fixed as far as syncing! It would seem as though the change in either processor or OS has solved the problem. I have no way of narrowing it down right now since this Intel machine won't run Tiger (AFAIK) and the G4 is currently out of commission. If I can get it running and put Leopard on it, I'll post here to let you know what I find out.

Nov 5, 2009 11:40 AM in response to KepiSW

I upgraded my itunes and my mac can no longer even find my ipod. I think it's first generation shuffle I don't think it's a 1gb. I'm not sure. It's old version. Any suggestions. I would just like to be able to access my ipod at all and I won't care about dubs or any of the other crap that everyone is having trouble with. I'll just be happy if I can find my ipod. Any help???

iTunes 8.1 breaks syncing with 2nd gen iPod shuffle

Welcome to Apple Support Community
A forum where Apple customers help each other with their products. Get started with your Apple ID.