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I'm almost embarrassed to post this: I can't re-order the songs in any playlists on my Mac. It's iTunes 12.1.0.50 on OSX Yosemite 10.10.2.

The playlists are all sorted in manual order. There doesn't appear to be anything wrong with them. They all play; each playlist, each song. It is a mixture of playlists I've created on this computer and ones I've synced from another. They are not shuffled. iTunes Match is enabled and not currently syncing. I've quit and restarted iTunes.

Just in case I've missed something, here's a screenshot:

Screenshot of arbitrary playlist from my iTunes

Help me Ask Different, you're my only hope.

  • I remember having this issue in iTunes for Windows once. Unfortunately I do not remember how I resolved the issue. – L.B. Dec 22 '16 at 13:14
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posted as answer to add pic…

This tells me it's shuffled right now; click it to turn off again.

enter image description here

Re-ordering should be as simple as dragging to a new position, but whilst it's shuffled it will appear to ignore you, as it's unlikely to recalculate the shuffle at that point.

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    Nope, I realized after I posted the screenshot that I happened to be shuffling. Turning off shuffle doesn't let me re-order. – drhayes Feb 19 '15 at 16:24
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Okay, so this is weird... OSX suddenly started to be unable to copy and paste in certain applications (Sublime Text 2 could cut/copy, but wouldn't paste anything, couldn't cut from Chrome then paste in Sublime, etc). I've had this issue before with Yosemite. I restarted, which I've used to fix the issue before.

Now I can re-order songs in iTunes. Related to clipboard stuff?! I'm at a total loss and don't feel like I've answered anything. Would love to get more insight into this.

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    Actually, drag-and-drop is tied in with the pasteboard system, so that might have something to do with it. Sorry I can't help you beyond that. – 0942v8653 Feb 19 '15 at 19:47
  • Confirming my suspicions is a good form of help. Thanks! – drhayes Feb 24 '15 at 2:56
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I had the same issue. I discovered that my iPhone 5S was connected via Wi-fi. Once I disconnected it, control of everything in iTunes returned.

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According to your screenshot, your sort order is with the numbers (position). I feel bad to ask, but what happens if you clicked on the header for "Name", "Artist" or "Album"? Does that sort them by name, artist and album respectively?

  • It does. The numbers should sort by "Manual Order" which is available under View > View Options (or Command-J). But, really, see my answer above. – drhayes Feb 24 '15 at 2:55
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So here's what I did to shuffle the order of my playlist.

  1. Select all the songs you want in the playlist

  2. Edit all their info so they have a matching category (artist, album, grouping, etc.)

  3. Create a smart playlist with the rule to include all items containing whatever matching info you chose.

  4. Select the limit to [any number higher than the number of songs in your playlist] items option with items selected by random

  5. Select OK

  6. You should have a smart playlist with randomized order. You can now copy this to a regular playlist if you'd prefer not to use a smart playlist

  • Thanks for the workaround. Turns out the pasteboard system on my laptop was inexplicably messed up and restarting fixed it. – drhayes Apr 6 '15 at 21:21
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I finally found the easy way to do this - on the top right corner you have a drop down list often set to 'Songs' or 'Playlist'. Just enter this menu and you can see the option 'Sort by'. Select 'Playlist order'. That should do it!

  • Thanks for answering this! It turned out I was having a seemingly-unrelated issue with my pasteboard. A restart fixed it. – drhayes Jan 21 '16 at 21:49
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Go into edit and put say 1 of 5, 2 of 5, 3 of 5 and so on in compilation. It took me ages to work this out. Worked for me.

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protected by bmike Dec 22 '16 at 13:03

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