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One of the handy things that you can do with data binding in WPF is that you convert the data as you pull it from the data source.The mechanism for this is the IValue Converter interface.
Frankly, thinking about this approach gives me headaches.
Here's what the XAML for that looks like: This code looks more complicated than it is. First note that we need to check explicitly if we're dealing with an enum type.
It's not possible to do this with a type constraint.
We need something that can map an enum constant to a boolean and back. While we're at it, let's make the class generic enough to handle all enumerations so we don't need a separate class for every enum: One inherent limitation of this technique is that you cannot use it to bind checkboxes to flag enums, because the converter can only convert a single value, not the combined state of all checkboxes.
You can't get around this by using , at least not in an intuitive fashion, because the binding is "the wrong way around": Multi Binding takes different values to produce one new value, so we'd need to bind the enum property in the view model to the checkboxes, rather than the other way around.