This is my List Context Menu:
If I have "Hide Windows items on file context menus (shift overrides)" Checked.... then the nested Lister Context Menu does not appear unless I am holding the Shift key until I hover over it.
In other words, I must keep the shift key held from the moment I right click, until the moment I hover over the "More..." submenu, otherwise it doesn't appear.
Also, I noticed that when I right click files, it takes a very long time for the right-click menu to appear since I have apparently installed many things over the years. I don't know which piece of software is slowing down my right click menu. Observe what I mean: Speedy vs Sluggish right click - YouTube
It would be nice if there was an option that allowed me to nest windows related context items into a submenu called "More..." like I have shown in the above screenshot, and this would allow the right click context menu to appear instantly since far fewer items will have to load.