So you’ve managed to get a foothold into the web server — now what? Privilege escalation can be an intimidating process for those unfamiliar with Linux systems or advanced penetration testing techniques. Servers are often cluttered with utilities, backups, and files; how do you find your way through to a root shell? Where are the first places an attacker might look for exploitable vulnerabilities? This slide deck will help you learn about common privilege escalation paths on Linux systems, including sticky bits, shell escapes, wildcard injections, and how to identify vulnerable services. Furthermore, it will illustrate several techniques for those looking to improve their security skills, with time for discussion afterward. (This was originally presented on February 22, 2010 at Day of Shecurity Boston 2019).