The toolbar cascade function seems to work conditionally in the popup container/toolbar. If you open the popup container, left-clicking a toolbar cascade arrow on a button closes the popup entirely. However, if you open the popup container and then pin it open, then the cascade toolbar arrows function normally.
Just in case it’s relevant, I have one toolbar living in a container for the popup. The middle mouse button calls up the container. Rhino 8.0.23304.9001, 2023-10-31