This article describes the design case of an instructional experience incorporating videos of mistakes for students to practice mistake detection and recovery skills. Learning from mistakes is often encouraged, but students may need practical support to address them effectively. The intention of this design is to facilitate adaptive cognitive and emotional responses to handling mistakes. This article documents two distinct but related formats of a mistake recovery design: a personal video recording and pre-recorded videos featuring fourth grade mathematics. These two formats evolved from personal experiences to become a classroom intervention. We trace this design process including the context, theory, and implementation experiences that shaped the design and discuss unforeseen obstacles and design alterations that arose during this process.