I tried it like this :
Private Sub DataGridView2_CellEnter(sender As System.Object, e As System.Windows.Forms.DataGridViewCellEventArgs) Handles DataGridView2.CellEnter
If DataGridView2.Rows.Count > 0 Then
CheckBox1.Checked = CBool(DataGridView2.Rows(e.RowIndex).Cells(0).Value)
End If
End Sub
You should notice that the Value of the Cell is refreshed when you leave the cell ...
Perhaps it helps you to get your code working ...
Edited :
To get the actual Value of a Cell like this you should call it like this :
chkTapeSealed.Checked = CBool(LoadingGrid.Cells(13).EditedFormattedValue)