Updating RibbonMenu at runtime

I am trying to update Winform's RibbonMenu's content when the menu is clicked (dropdowned) at runtime. I have a RibbonCheckbox inside this RibbonMenu, and every time I open the menu, I want to check for certain conditions and set the checkbox's Checked status accordingly.

I am aware of setting Dynamic = true and ItemsLoading event, however this is only called once when the RibbonMenu is loaded the first time. How can I update the Checkbox status every time the menu is clicked?

Thank you.