Positioning yourself as a man-in-the-middle (MitM) is a powerful situation to leverage during a security assessment. Unfortunately, in some situations, leveraging an active MitM position is difficult. There are existing proxies that try to alleviate these issues but they all seem to suffer from a flaw that makes using the tool undesirable. MitM-VM and Trudy are a complimentary set of tools that are designed to address several issues with existing proxies. Together they enable easy-to-setup and powerful man-in-the-middle positions.Why build these tools? Modifying custom binary protocols on the fly while sitting between an embedded device and a server is usually a slow process that involves sniffing legitimate traffic and then rebuilding packets programmatically. Trudy makes this process easy by enabling Burp-like features for generalized TCP traffic.