diff --git a/plugins/osx/osx.plugin.zsh b/plugins/osx/osx.plugin.zsh
index 2eea0d8e..d366f1fc 100644
--- a/plugins/osx/osx.plugin.zsh
+++ b/plugins/osx/osx.plugin.zsh
@@ -177,12 +177,43 @@ function itunes() {
 		vol)
 			opt="set sound volume to $1" #$1 Due to the shift
 			;;
+		shuf|shuff|shuffle)
+			# The shuffle property of current playlist can't be changed in iTunes 12,
+			# so this workaround uses AppleScript to simulate user input instead.
+			# Defaults to toggling when no options are given.
+			# The toggle option depends on the shuffle button being visible in the Now playing area.
+			# On and off use the menu bar items.
+			local state=$1
+
+			if [[ -n "$state" && ! "$state" =~ "^(on|off|toggle)$" ]]
+			then
+				print "Usage: itunes shuffle [on|off|toggle]. Invalid option."
+				return 1
+			fi
+
+			case "$state" in
+				on|off)
+					# Inspired by: http://stackoverflow.com/a/14675583
+					osascript 1>/dev/null 2>&1 <<-EOF
+					tell application "System Events" to perform action "AXPress" of (menu item "${state}" of menu "Shuffle" of menu item "Shuffle" of menu "Controls" of menu bar item "Controls" of menu bar 1 of application process "iTunes" )
+EOF
+					return 0
+					;;
+				toggle|*)
+					osascript 1>/dev/null 2>&1 <<-EOF
+					tell application "System Events" to perform action "AXPress" of (button 2 of process "iTunes"'s window "iTunes"'s scroll area 1)
+EOF
+					return 0
+					;;
+			esac
+			;;
 		""|-h|--help)
 			echo "Usage: itunes <option>"
 			echo "option:"
 			echo "\tlaunch|play|pause|stop|rewind|resume|quit"
 			echo "\tmute|unmute\tcontrol volume set"
 			echo "\tnext|previous\tplay next or previous track"
+			echo "\tshuf|shuffle [on|off|toggle]\tSet shuffled playback. Default: toggle. Note: toggle doesn't support the MiniPlayer."
 			echo "\tvol\tSet the volume, takes an argument from 0 to 100"
 			echo "\thelp\tshow this message and exit"
 			return 0