Delving into the world of Historical European Martial Arts (HEMA), this chapter discusses the training, coaching, and intricacies of sword fighting based on historical documents. From understanding the concept of 'measure' in fencing to grappling with teaching offensive skills and developing situational awareness, the conversation highlights the challenges and nuances of mastering sword martial arts. The chapter also touches on the popularity of the long sword, characteristics of sword training, and the evolving approach to learning HEMA through historical manuscripts.