In recent years, defensive technologies have moved past the traditional filtering and anomaly detection at Layer 3 and 4, and deep packet and payload inspection have become more prevalent. As penetration testers, it's important to understand how to adapt exfiltration techniques to exploit the limitations next generation firewalls, application aware proxies, URL filters, and data loss prevention packages have. This talk will cover several techniques for building payloads to bypass all of these technologies, from basic file encoding to making and proxying outbound connections as legitimate applications. A completely revamped and extended version of Fireaway, a tool originally designed to bypass next generation firewalls, will be released as part of the talk as well.