Q: I can’t seem to move songs around within certain playlists. Is there a song limit for playlists? It seems that in a longer playlist I can’t rearrange songs but in shorter ones I can. Any suggestions?
A: To be able to manually re-order songs in a playlist, you must not be sorting the playlist in any way and you must not have Shuffle mode enabled for that playlist. A sorted or shuffled playlist cannot be manually reordered since either of these settings specify a pre-determined order for the tracks in the playlist.
You can tell if you are sorting the playlist by another column simply by looking at the column headings—the current sort column will be highlighted in blue.
To return the playlist to its natural “unsorted” order, simply click on the left-most column heading, above the first number column. This column heading will turn blue and the playlist will return to its default order.
Further, the Shuffle option is set on a per-playlist basis rather than globally, so you should ensure that this is turned off as well. You can check this by looking at the buttons in the bottom-right corner of the iTunes window. If Shuffle mode is enabled for the current playlist, the Shuffle button will be highlighted in blue:
Simply click on the Shuffle button to disable Shuffle mode.
As an aside, Shuffle mode also behaves a bit differently depending on whether you are sorting the playlist by another column or not. When the playlist is not sorted, enabling Shuffle will actually re-arrange the track listing into a random order, while disabling Shuffle will return the tracks to their original order. When sorting the playlist by another column, however, enabling or disabling Shuffle mode leaves the playlist displayed in its sorted order, however when Shuffle is on the tracks will actually play back in a random order.
Once you are sorting the playlist by its natural sort order, you can then reorganize the tracks as desired simply by selecting a track and dragging up or down in the playlist to change its position.
If you want to reorganize the tracks from a sorted or shuffled order you can copy the currently-displayed track order to the default play order simply by sorting the playlist how you would like, and then right-clicking on it in iTunes and choosing “Copy to Play Order” from the pop-up menu.