Thank you so much for your help, here is my current code but it isn't prompting for the flag, any ideas? Also note I have a current script on top for BCC'ing my gmail address on all sent items, but they shouldn't be affecting each other.
Here is my current code, any help is appreciated:
Private Sub Application_ItemSend(ByVal Item As Object, Cancel As Boolean)
Dim objRecip As Recipient
Dim strMsg As String
Dim res As Integer
Dim strBcc As String
On Error Resume Next
' #### USER OPTIONS ####
' address for Bcc -- must be SMTP address or resolvable
' to a name in the address book
strBcc = "fakeemail@gmail.com"
Set objRecip = Item.Recipients.Add(strBcc)
objRecip.Type = olBCC
If Not objRecip.Resolve Then
strMsg = "Could not resolve the Bcc recipient. " & _
"Do you want still to send the message?"
res = MsgBox(strMsg, vbYesNo + vbDefaultButton1, _
"Could Not Resolve Bcc Recipient")
If res = vbNo Then
Cancel = True
End If
End If
Set objRecip = Nothing
End Sub
Private Sub Application_Startup()
Option Explicit
Private WithEvents olSentItems As Items
Dim objNS As NameSpace
Set objNS = Application.Session
' instantiate objects declared WithEvents
Set olSentItems = objNS.GetDefaultFolder(olFolderSentMail).Items
Set objNS = Nothing
End Sub
Private Sub olSentItems_ItemAdd(ByVal Item As Object)
On Error Resume Next
Dim prompt As String
prompt$ = "Do you want to flag this message for followup?"
If MsgBox(prompt$, vbYesNo + vbQuestion + vbMsgBoxSetForeground, "Add flag?") = vbYes Then
With Item
.MarkAsTask olMarkThisWeek
' sets a due date in 7 days
.TaskDueDate = Now + 7
.ReminderSet = True
.ReminderTime = Now + 6
.Save
End With
End If
End Sub
(Because you are the sender) 
