Your question is a little unclear. But as I can guess you are using binding in WinForms? If that is the case you probably use a
BindingSource[
^], which can easily be reset with the Reset Method as follows:
myBindingSource.Reset(false);
Also, when looking at the Property Grid for any bound Control under the Bindings section -> Advanced you can choose any of the following update methods: OnValidation and OnPropertyChanged. For checkboxes you probably want OnPropertyChanged. This causes your BindingSource to update whenever it is checked or unchecked rather than when it loses focus.
Hope this solves the problem.