Here's what I ended up with... seems to work great for me. - Russ Private Sub Application_ItemSend(ByVal Item As Object, Cancel As Boolean) 'Declaration Dim myItems, myItem, myAttachments, myAttachment As Object Dim myOrt As String Dim myOlApp As New Outlook.Application Dim myOlExp As Outlook.Explorer Dim myOlSel As Outlook.Selection Dim Response As String On Error Resume Next 'work on selected items Set myOlExp = myOlApp.ActiveExplorer Set myOlSel = myOlExp.Selection 'for all items do... For Each myItem In myOlSel With myItem If Not myItem Is Nothing Then Response = MsgBox("Do you want to mark this message Waiting For Reply?", vbYesNoCancel, "Category?") = vbYes If Response = True Then .Categories = "Waiting For Reply" .FlagRequest = "Waiting" .Save End If If Response = False Then .Categories = "Complete" .ReminderSet = False .TaskCompletedDate = Date .Save End If End If End With myItem.Save Next 'free variables Set myItems = Nothing Set myItem = Nothing Set myOlApp = Nothing Set myOlExp = Nothing Set myOlSel = Nothing End Sub