Documentation for using a checkbox with a gridview has the following statement:
Because a check box can display only a selected or an unselected state, a CheckBoxField object can be bound only to a field with a Boolean data type or a string that can be parsed by Parse.
No example has yet been found to explain how using Parse to control the value of theis done. Interestingly enough I can find a fine example for the unlikely scenario of embedding a bulleted list in a grid cell.
How can get a Y/N (or Y/blank) value into the checkbox field?
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