The primary purpose of this workshop is to discuss the challenges and requirements in control, dynamics, optimization, and system design for fielding legged robotics in real-world scenarios. These types of robotic platforms have an enormous potential for swaths of applications, particularly where mobility challenges limit the application of more traditional ground robots. We will use this workshop to present discussion pieces and foster conversation on the true challenges limiting the fielding of legged robots. The workshop will feature invited pioneers in the legged robotics community to discuss what they see as technical challenges limiting legged technology. Further, several speakers will feature live demonstrations of their hardware platforms, giving attendees in-person physical examples of these concepts in action.