Решено: Активировать IE по идентификатору процесса
strWebSite = "file://C:/Windows/System32/calc.exe"
Set ie = GetObject ("", "internetexplorer.application")
ie.Navigate2 strWebSite
WScript.Sleep 500
Set WshShell = WScript.CreateObject("WScript.Shell")
Set Processes = GetObject("winmgmts:").InstancesOf("Win32_Process")
intProcessId = ""
For Each Process In Processes
If StrComp(Process.Name, "iexplore.exe", vbTextCompare) = 0 Then
intProcessId = Process.ProcessId
Exit For
End If
Next
Set WshShell = WScript.CreateObject("WScript.Shell")
WshShell.AppActivate intProcessId
WScript.Sleep 3000
WshShell.SendKeys "{TAB}"
WshShell.SendKeys "{ENTER}"
WScript.Sleep 3000
WshShell.SendKeys "{TAB}"
WScript.Sleep 3000
WshShell.SendKeys "{TAB}"
WshShell.SendKeys "{ENTER}"