Devi crearti una classe che intercetta il popolamento delle celle e in quel preciso momento sostituire il valore con degli asterischi, naturalmente devi costruirti il datagrid a manina ed ereditare la DataGridTextBoxColumn
codice:Public Class ColoredTextBoxColumn Inherits DataGridTextBoxColumn Public Sub New() End Sub Protected Overloads Overrides Sub Paint(ByVal graph As Graphics,ByVal rectbounds As Rectangle, ByVal curmngrSrc As _ CurrencyManager, ByVal RowNumber As Integer, ByVal _ ForeColorBrush As Brush, ByVal BackColorBrush As Brush, _ ByVal AlignmentRight As Boolean) Dim o As Object o = Me.GetColumnValueAtRow(curmngrSrc, RowNumber) If Me.HeaderText = "Colonna che voglio nascondere" Then If (Not (o) Is Nothing) Then Dim cellValue As String cellValue = CType(ObjVal, String).ToString ecc... ecc... qui va il tuo codice di sostituzione MyBase.Paint(graph, rectbounds, curmngrSrc, RowNumber, _ ' BackColorBrush, ForeColorBrush, AlignmentRight) end sub end class

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