You can check box to enable Voice Over, and all appears well but then greys out, and test of shuffle after playlist sync proves no VO-
Worked prior on a diff pc; both pc's at latest itunes and shuffle version(s)
The pc n o w is Win7 64 and prior working system was Win Vista 32
Archived - iPod shuffle (4th generation): Enabling and using VoiceOver
Enabling VoiceOver in iTunes for iPod shuffle (4th generation) allows you to hear the names of songs, artists, and playlists spoken when listening to content on iPod shuffle. VoiceOver also tells you battery status and other messages. You can enable VoiceOver when you first set up your iPod with iTunes, or you can set it up later in the Summary button, in iPod settings, in iTunes. When you select the option to enable VoiceOver in the iPod Setup Assistant or in the Summary button, you will be guided through the process of installing the VoiceOver Kit.