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Level 1

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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

Apr 6, 2009 3:10 PM in response to Jason L

thanks for your response, but unfortunately 8.1.1 doesn't correct the problems either. do you know of any other potential solutions? thanks

Logainne

Level 1

0 points

Apr 6, 2009 4:31 PM in response to KepiSW

Thanks SO MUCH for posting this. I have a 2nd gen iPod shuffle and a MacBook Pro and thought I was losing my mind. I guess I am still losing my mind, but at least now I know it's on account of Apple. Ugh.

Apr 6, 2009 6:01 PM in response to KepiSW

This situation is a total disgrace. They might have considered posting a warning: "Caution: if you accept this upgrade, your hardware will break."

It is a situation worthy of Microsoft, not the Apple of legend.

Apr 6, 2009 8:11 PM in response to KepiSW

My 2nd Gen Shuffle's syncing behaviour has not changed with the upgraded 8.1.1 iTunes. So sad.....

Apr 6, 2009 9:33 PM in response to Joe Canadian

8.1.1 FTL

My 2nd Gen. Shuffle still misbehaving (just as it has since iTunes 8.1)

Apr 7, 2009 10:04 AM in response to Thomas Tibbitts

Try a "restore" next time you sync your Shuffle in iTunes.
I was also experiencing the problems in 8.1. Found the same in 8.1.1. Then I restored the Shuffle's firmware and it all seems to be working normally (for me),

Apr 7, 2009 2:41 PM in response to Larry Duran

Restoring the firmware didn't fix it here... none of the metadata ever gets synced right anymore and the play order is still messed up. I tried created a mirror playlist, hoping that would help, but that didn't do anything either.

Ugh.

Apr 7, 2009 2:42 PM in response to Jason L

Do not install 8.1.1!

Another new Feature of this "upgrade", is that I can no longer create lists from the Shuffle itself.

I used to be able to drag a selection of tracks from the unit, to an existing play list, which would allow me to at least manually compare tracks, and manipulate their order.

I can no longer even do this with the upgrade!

Also, as has been the case for the last two upgrades, I can no longer play selections on the device playlist itself when it is attached via USB.

On the plus side: it no longer hangs iTunes periodically like it used to when doing this.

On the minus side: I cannot reset tracks to the beginning, or monitor the current location in the file, or see the amount of unheard material from within iTunes.

And since there is no display on the Shuffle, "Houston, we have a problem."

Still patiently waiting for basic functionality to return.

Apr 7, 2009 4:09 PM in response to Andrew Heiss

OK, did the reset as Larry suggested.

It reset the Shuffle using the current iTunes version, and I have much improved performance since my last post.

I can play tracks on the iPods playlist while plugged in with USB.

Playcounts now update for me.

I can add songs on the iPod's list to a new iTunes playlist (sometimes).

It seems to remember much more effectively the playhead position on a track.

Negatives:

Still allows duplicates without a warning.

Doesn't seem to allow or remember sorting of iPod track order within iTunes (date, title, or artist).

Plynke

Level 1

0 points

Apr 7, 2009 9:12 PM in response to KepiSW

I found another fix. After I downgraded back to 7 I could play from my itunes again, but it still wouldn't sync the stopping point when I listen to half a chapter in my audio books. I fixed this! You have to right click on the song and go into "Get Info". Under the options tab there is an option for "Remember Playback Position". It used to do this automatically, but I guess it broke with the upgrade. Hope this helps someone!

Apr 8, 2009 3:23 PM in response to KepiSW

I was fortunately able to roll back to 8.0.2 and recreate my library and everything is back to normal. I'll definitely be avoiding all future updates until they find a fix.

Apr 10, 2009 10:14 AM in response to Andrew Heiss

I generally always go for an upgrade to Apple software. No longer.

I don't do podcasts, I have my shuffle to... listen to music. In point of fact, I have only recently noticed issues... but I think MY issues may have started with 8.1.1... but onto the details.

I have a very specific set-up that I use. I have a smart playlist that lists only files that have 0 as the play count. I fill my 2g shuffle from this list. Each time I sync, the files I have listened to fall of this list. I always "fill randomly" and play in continuous mode. Thus I get shuffled songs that won't get added back in until ALL my songs are played... at which time I reset the play counts back to zero.

So the list of songs on my shuffle will show (in iTunes) exactly what order they will play in... remember they are randomly added to start with. Thus, when I sync again, I'll see the date of sync and a 1 play count at the top of the list.

What I have seen recently is that it seems to want to skip files at the top of the list, but WILL tag them as having been played. The last time I did this, I noticed it didn't start with the top listed song, but one under it. Even a triple click brought mew to song #2. After a couple dozen songs, I synced again. Wouldn't you know, my #1 song was listed as being played, however, it did NOT play.

First, has anyone seen anything like what I am seeing? Like I said, I've noticed it in the past 2-3 weeks, so maybe it's something that started with 8.1.1???

user2009

Level 1

8 points

Apr 10, 2009 4:27 PM in response to KepiSW

Well count me in on this issue as well. Wow, never had to post here before this week. I all but pulled my hair out with my 2nd gen blue last night....i tried all my computers, of which are running the most recent iTunes. To to let people know, i have a 3rd gen and a 1st gen shuffle as well. Im about ready to go back to the 1st gen and return both the 2nd & 3rd gens this weekend!!!!!

1 issue last week-still happening with the 3rd gen
1 issue this weekwith the 2nd gen.
next week??????????????

Apr 12, 2009 12:54 PM in response to KepiSW

iTunes 8.1.1, experiencing all problems with "update," namely podcasts, syncing, play counts, duplicate tracks, track order, etc. Pity.

Apr 13, 2009 12:33 PM in response to Larry Duran

UPDATE
The "restore" did make things a bit better, but my 2G Shuffle is still not working properly. Still having trouble with syncing. It still doesn't act like a "playlist in my pocket" which is what it should be. Unless I delete a song after syncing to force a "real sync" playorder and all the rest are still a mess. It doesn't seem to be mixing up songs though.
Every time I sync I love my Shuffle a little less. And every time I realize how Apple messed it up I hate Apple a lot more (and I'm what you'd call a big fan).
I have NEVER BEEN MORE DISAPPOINTED IN APPLE.

iTunes 8.1 breaks syncing with 2nd gen iPod shuffle