The following VBA code gets stuck at the While loop:
Sub SaveAsText2(MyMail As MailItem)
    ' Export email (with PowerShell script in body) as a text file
    MyMail.SaveAs "c:\scripts\outlook.ps1", olTXT
    
    ' Create a response email
    Dim reMail As Outlook.MailItem
    Set reMail = MyMail.Reply
    ' wait till transcript is available
    Dim MyFSO As FileSystemObject
    Set MyFSO = New FileSystemObject
    
    If MyFSO.FileExists("C:\Scripts\email_transcript.txt") Then
         ' This bit works correctly
         ' MsgBox "The file Exists"
    Else
         ' This bit works correctly as well
         ' MsgBox "The file Does Not Exist"
    End If
    ' This part fails to evaluate regardless if the file is there or not
    While Not MyFSO.FileExists("C:\Scripts\email_transcript.txt")
        ' WScript.Sleep 1000
         Application.Wait (Now + TimeValue("0:00:01"))
         
         MsgBox "The file Does Not Exist"
    Wend
    Set fs = CreateObject("Scripting.FileSystemObject")
    Set a = fs.CreateTextFile("c:\scripts\testfile.txt", True)
    a.WriteLine ("This is a test.")
    a.Close
    
    ' attach the transcript and send it back
    reMail.Attachments.Add "C:\Scripts\email_transcript.txt"
    reMail.Send
    
    MyFSO.DeleteFile ("C:\Scripts\email_transcript.txt")
End Sub
If the email_transcript.txt file exists, then the While loop gets skipped (which is correct) and the rest of the script runs. No issues here.
If the email_transcript.txt file does NOT exist, then the While loop will wait until the file exists. However, even when the file exists at this point, the While loop never validates and therefore it doesn't process the rest of the script.
The MsgBox in the While loop doesn't trigger when the file does NOT exist.