When I bind a Linq-to-sql query to a datagridview (using a BindingSource in between), the columns are sortable by default. However, this does not seem to be the case for boolean
In VS2012 in the designer you can also set the SortMode.
Right-click on the DataGridView and go to "Edit Columns".
There's a drop-down for SortMode with a choice of NotSortable, Automatic, and Programmatic.
It appears that the default for most columns is Automatic, but for checkboxes (boolean) columns the default is NotSortable.