Pivoting, tunneling, and redirection are essential skills that separate the junior and senior operators in the offensive security landscape. This workshop describes various techniques used to creatively route traffic through multiple network segments. Various tools and techniques will be discussed and demonstrated. Attendees will be able to practice these skills in a provided cyber range during and after the workshop. These are essential skills for every pentester, bug bounty hunter, and red team operator. But that's not all! Defenders will learn techniques for detecting this sort of suspicious traffic.