iTunes Extras not playing in iTunes 12.13.13 under Windows 11 Pro (23H2)

I haven't seen this for some time so my memory is hazy, but I recall an issue a while back where iTunes didn't unpack the downloaded extras package correctly and move into the correct location within the movies folder. It should be a .zip file with a different file extension. Compare the layout with an extras package that works.

tt2

I've seen this issue reemerging for many (dozens) recently, resulting with often random explanations of what's actually going on, no supported diagnoses, and no successful solutions being offered, including from Apple Support, and then nothing but dead-air....

Nevertheless, I think you're referring to the (movie title)-iTunes Extras (v.n.n).ite folder/file extension, but I think Apple hasn't (visibly) packed those with downloaded movies for a while, in my experience.

The actual iTunes for Windows Extras content appears to be "live-streamed" from some Apple server in what the newly opened player refers to as "Live Broadcast" and "Live" (on the iTunes Media Library page atop a greyed-out progress bar with empty time markers) in the playback control areas when playback is unsuccessful, i.e., black-screen and no audio. In addition, the Pause/Play symbol is shown as a white square (denoting playback failure?) rather than the standard Pause double vertical lines.

However, I find that Extra playback is now only randomly successful, over time, among all my movie library titles, and when it is successful, no reference to "Live" or "Live Broadcast" is made in the opened player and normal playback controls are displayed. I also observe no connection to Extra playback success and when the movies were purchased, their vintage, or if they were downloaded or not. In one case, I purchased a movie trilogy all at the same time and Extra playback only works on one! (And yet, all the Extras play reliably on my Apple devices...from iPhone, iPad, MAC Pro, MAC mini, to Apple TV.)