When the machines rise up and take away our freedom to communicate we're going to need a way out. Exfiltration of data across trust boundaries will be our only means of communication. How do we do that when the infrastructure we built to defend ourselves is the very boundary we must defeat? We use the same pathways we used to, but bend the rules to meet our needs. Whether its breaking protocol, attaching payloads, or pirating the airwaves we'll find a way. We'll cover using a custom server application to accept 'benign' traffic, using social and file sharing to hide messages, as well as demo some long range mesh RF hardware you can drop at a target for maximum covert ops. Bio: Willa Cassandra Riggins is a penetration tester at Veracode, and was previously part of the Lockheed Martin CIS Red Team. She started her career as a developer and pivoted into security to help fight the pandemic that is developer apathy. Her background spans the software development lifecycle, but her heart is in root shells and crown jewels. She can be found making things at FamiLAB in Orlando, hacking at the local DC407 meet-ups, staffing the socials at BSides Orlando, and marketing all the things at OWASP Orlando.