C# Null-Coalescing Operator with DBNull – How to Use

Not like that, no. The types have to match. The same is true for the ternary.

Now, by "match", I don't mean they have to be the same. But they do have to be assignment compatible. Basically: in the same inheritance tree.

One way to get around this is to cast your string to object:

var result = (object)stringVar ?? DBNull.Value;

But I don't like this, because it means you're relying more on the SqlParameter constructor to get your types right. Instead, I like to do it like this:

cmd.Parameters.Add("@theParam", SqlDbTypes.VarChar, 50).Value = theParam;
// ... assign other parameters as well, don't worry about nulls yet

// all parameters assigned: check for any nulls
foreach (var p in cmd.Parameters) 
{ 
    if (p.Value == null) p.Value = DBNull.Value; 
}

Note also that I explicitly declared the parameter type.

A couple of (very) simple generic helper methods might at least concentrate the test into one piece of code:

static T FromDB<T>(object value)
{
    return value == DBNull.Value ? default(T) : (T)value;
}

static object ToDB<T>(T value)
{
    return value == null ? (object) DBNull.Value : value;
}

These methods can then be used where appropriate:

private void UpdateRowEventHandler(object sender, EventArgs e)
{
    AdditionalSupport.UpdateASRecord(year, studentID, 
        FromDB<Boolean?>(grdMainLevel1.GetFocusedRowCellValue(colASRequiresSupport)));
}

internal static void UpdateASRecord(
        string year,
        string studentID,
        bool? requiresSupport)
{
    List<SqlParameter> parameters = new List<SqlParameter>();

    parameters.Add(new SqlParameter("@year", SqlDbType.Char, 4) { Value = year });
    parameters.Add(new SqlParameter("@student_id", SqlDbType.Char, 11) { Value = studentID });
    parameters.Add(new SqlParameter("@requires_support", SqlDbType.Bit) { Value = ToDB(requiresSupport) });

    //execute sql query here to do update
}