Getting In The Middle Un-patched and out-of-date software is a common attack vector for penetration testers and attackers alike. Applications such as Adobe Reader and Microsoft Office are popular targets due to their widespread use on Windows systems and user’s willingness to click on just about anything. They both have the ability to perform self-updates, similar to the operating system, but limited to one particular software package. However, what happens when the software update process itself is insecure? Enter a program called "evilgrade", which exploits this process to install software of an attacker's choosing. For this attack to succeed, the victim machine must be the victim of a Man-In-The-Middle (MITM) attack.