Hi Thomas,
Thanks for the update.
You should use ParentBarItems in place of BarItem where a list of child BarItems needs to be shown, and Checked property of the BarItem can be toggled upon click to make it behave like a checkBox.
I have attached a sample to demonstrate how PopupMenu can be associated with a control. Refer the sample and let me know if this helps.
PopupControlContainer is intended to host objects of type 'Control', and is not the best way to implement popup menus.
Regards
Vallarasu S.
ContextMenuSample_aef47e4.zip