In iTunes 10, you could skip to the next/previous track when Repeat One was turned on. In 11 & 12, they assume that by “skip ahead”, you somehow mean “rewind this track”.

This really bothers some people.
Do not judge us, we have our reasons!

And here’s one way to fix it.

It took some work, but I finally came up with some AppleScript to handle this. Basically, we’re checking to see if Repeat One is on. If it is, we quickly disable it, skip to the next (or previous) track, and then turn it back on. Apple borked the old way of doing this (same with shuffle), so we’re using menu bar items instead.

-- This script lets you skip songs in iTunes 11/12 even if repeat one is on

tell application "System Events"
	tell process "iTunes"

		-- Find out if repeat one is on
		-- This finds out if the menu item is checked
		set isRepeatOneOn to (value of attribute "AXMenuItemMarkChar" of menu item 3 of menu 1 of menu item "Repeat" of menu 1 of menu bar item "Controls" of menu bar 1 as string) ≠ ""

		if isRepeatOneOn is true then

			-- Set repeat to ALL
			click menu item 2 of menu 1 of menu item "Repeat" of menu 1 of menu bar item "Controls" of menu bar 1

			-- Skip to previous track...
			click menu item "Previous" of menu 1 of menu bar item "Controls" of menu bar 1

			-- Need this, or the next step happens too fast
			delay 0.1

			-- Reactivate Repeat One
			click menu item 3 of menu 1 of menu item "Repeat" of menu 1 of menu bar item "Controls" of menu bar 1

		else
			-- Just skip to previous track
			click menu item "Previous" of menu 1 of menu bar item "Controls" of menu bar 1
		end if

	end tell
end tell

You can copy/paste that, or you can just download the script files here.
There’s one script for skip ahead, and one for skip back.

Wait—how do I use these?

Valid question. They’re not all that useful, really—unless you assign them to hotkeys.

Head on over here to Mac OS X Tips for ways and examples to set hotkeys to run AppleScripts.

Personally, I used Quicksilver to control iTunes for years, but now I use Alfred 2 (with Powerpack.)

(Since it’s not super obvious, let me know in the comments if you’d like help setting up either of these scripts using Alfred 2.)

iTunes 10. Good stuff. But I’m really surprised that Apple — who are known for their design expertise — would not only violate a well-known design convention, but their own well-known design convention with those stoplight control buttons. It may seem like a simple annoyance, but multiply it by 1000 times over the course of a week or a month, and you have a fairly irritating problem.

Fortunately, putting those buttons back the way they should be is pretty easy. (Mac only)

1. Close iTunes if it’s open.
2. Open up Terminal.
3. Copy/paste this line into it:

defaults write com.apple.iTunes full-window -1

4. Mash Enter.

Done. Re-open iTunes and enjoy.