Gaining Initial Access and Outsmarting SmartScreen
I’ve had a number of people ask me what approaches I have taken to secure that initial foothold on a machine/network during a pentest engagement. Well, the blunt and honest answer to that question is…it depends 😸 Initial access comes in many forms and depending on the type of pentest engagement, you will be afforded or NOT afforded various types of “lures” you can use to acquire that first foothold. Most clients are open to the pentest team exhausting all their resources and offensive tooling to truly assess the client’s security controls. If not they should be. Because in a real world attack, you better believe the threat actor will not hold back! In today’s post, I’ll be going over a very traditional approach to achieving initial access using email as our attack vector of choice. I’ll go over various ways to send the email (gui and non-gui) and using attachments versus links. I’ll also explain how to contend with MOTW (Mark of the Web) and SmartScreen security restrictions on your downloaded payloads for the modern Windows 11 environment.
