The Turbine ContextMenu isn't a Control or ScrollableControl, it's just an Object so it doesn't have any of the functionality (like size and position methods) that would normally allow you to add a scrollbar. You'd have to build your own menu class which is a bit of a pain.
Can you instead group some of your functionality into submenus and build a two tier menu where you use one context menu as your main menu and its MenuItems pop up submenus where needed which would also be a context menus (kind of like how the in-game system menu works)? Then you would have the benefits of auto positioning and visibility control without having to build your own menu class.
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