iTunes 8.1 hates my iPod Shuffle (rev1)

I got bitten back when iTunes 7 first came out. It took quite a few versions before I could upgrade from iTunes 6 because the handling of my iPod Shuffle (rev1) was problematic.

It has happened again.

This time it’s iTunes 8.1 and the behaviour is very strange indeed.

Here is my iTunes workflow.

Process:
1) Plug in iPod Shuffle. iTunes opens and shows the shuffle playlist.
2) Sort by last played.
3) Select everything played now*, handily sorted to the top.
4) Sort by order (this reveals any songs I skipped over). If there were skipped songs, add them to the selection and drag the lot over to a holding playlist.
5) Click Autofill. While waiting for this to complete, process the holding playlist.
6) Click Eject.
7) Quit iTunes.

* iPod Shuffle does not record the last played time so iTunes puts in the sync time for any songs that were played. It’s not an ideal solution but it’s better than what we had when the shuffle first came out (last played was not updated at all).

The point of the holding playlist is for me to be able to change things about songs. Usually it’s because I don’t like a song anymore but I’ll also use it to notify myself of problems in audio (eg. bad panning).

The sorting bit requires that I listen to songs “in order” on the iPod. Since iTunes creates a randomized playlist this is fine (no sense in randomizing a randomized list). I have a fairly complicated playlist system setup so my music rotates onto the shuffle more or less frequently based on ratings and last played dates. Perhaps similar to the “play higher rated songs more often” but much more tuneable.

So after installing iTunes 8.1, I noticed a problem. When I sorted the playlist, the songs I had been listening to were not at the top. This has occasionally happened in the past due to the iPod randomly deciding to start in the middle of the playlist but a soft reset of the iPod (press play 3 times quickly) was enough to fix that. With iTunes 8.1 the problem was consistent. Actually, no matter how I looked at it I could not discern a pattern to how the on-screen view of the list was translated into what the device played. When I synced, the on-screen list changed such that the songs the iPod played were in order, though at the wrong end of the playlist. Occasionally I have had the on-screen view in iTunes fail to match the device but “Copy to play order” always fixed this. Now it doesn’t seem to do anything.

I have no idea what is going on. It’s like there is some kind of randomization going on underneath the covers that I cannot control or turn off. I have reverted back to iTunes 8.0.2 and now all is good again. Sadly, my playlists have been set back a few days but I suppose it could have been worse. You generally have to revert to the saved iTunes Library when downgrading. Luckily the only changes to my library in that time were a few days of last played updates.

About a1291762

I'm a software developer by trade and a musician by heart. I'm a techno-gadget freak and I dabble in photography. I'm married with two kids, we drive Toyotas and use Macintoshes.
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6 Responses to iTunes 8.1 hates my iPod Shuffle (rev1)

  1. Anonymous says:

    I have one of the old 0.5 GB Shuffles (long and skinny with an actually USB connecting port–I will never buy a new Shuffle that doesn’t have one) software version 1.1.5 and iTunes version 8.1 (50) running on a Mac Mini running OS 10.5.2. I was having the same (I think) problem. I would list to songs on the Shuffle, then I would connect the Shuffle to my computer, and the “Last Played” tags did not seem to update. Well, today I tried it, and it worked fine. I changed nothing–updated no software.

    I don’t understand it. But, you might want to give 8.1 another day in court.

  2. tootill says:

    I’m confused too. I’ve had a 1GB 2G shuffle since they first came out and synching to iTunes has always updated my “Last Played” date. Most of my play lists are based on this behavior. Now synching updates the “Last Played” date of the top songs in the list, not the songs I actually listened to. In other words if I listen to 2 songs on my Shuffle, iTunes will update the date on the first 2 songs listed which will not match the actual songs I listened to! Is anyone else seeing this?

  3. a1291762 says:

    Yes, this is exactly the behaviour that I am seeing.

    Sadly, iTunes 8.1.1 does not help the situation at all.

    You can downgrade to iTunes 8.0.2 but of course, you lose any changes made to your library since you upgraded to 8.1.

    To downgrade you need to remove /Applications/iTunes.app and /Library/Receipts/iTunesX.pkg. Then you can install using the 8.0.2 installer (which you can find on the internet). You also need to replace ~/Music/iTunes Music/iTunes Library with the latest file from Previous iTunes Libraries.

  4. tootill says:

    Thanks – that worked. Other than taking some of my ratings and play counts back to the middle of March, everything is working like a charm.

  5. tootill says:

    I just spoke with Apple Support. It turns out 8.1 requires XP SP3 or it’s “unpredictable” (I’m running SP2). So the solution is either to go back to iTunes 8.0.2 or upgrade XP to SP3.

  6. a1291762 says:

    The Apple support guys lied to you.

    There is no functional difference between XP SP2 and SP3, just a heap of hotfixes.

    Also, I have a Mac. The problem is in iTunes, the platform has nothing to do with it.

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