ContextMenuStrip and mouse wheel
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Since this is an old question you probably won't need this but just in case and for future reference. You can simulate the up and down keys to scroll it, its far from ideal , but it has to write its own ContextMenuStrip to handle the scroll wheel. Mouse scroll toolbar menu items
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Adding a lot of items to the CMS to scroll completely defeats the purpose of the context menu. Don't create a user interface that is difficult to use and requires the user to scan several dozen items. Your users will dislike your program with passion and will find out where you live.
CMS supports submenus. Classify your menu items.
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