About the checkbox: The original developer and several other developers considered this proper behavior of the datatype. From their point of view no input is also input. Hence, the required field is meaningless and therefore it doesnt do anything. We have decided to change this behavior for the checkbox field so required means "you are required to check the field". The bug is reported here: http://ez.no/community/bugs/checkbox_does_not_do_validation The fix should be pretty simple.
Enums will obviously not work as the datatype doesn't support info collection. You should be able to do this with some of the other datatypes that support radiobuttons though.
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