“How can my students sing every song I give them, but totally ignore the dynamic markings?” “Why is it that my students can identify dynamic markings on an assessment and yet not perform these skills when singing with or without directive cues?” “When and Where does this transfer of musical knowledge into musical skills take place?” These are questions that have puzzled me in my years of teaching middle school choir. Taking into consideration that the mindset of the young adolescent is quite malleable and yet there is an inconsistent transferring of their musical knowledge into a performance skill-set. The students in this study come from various ethnic and socio-economic backgrounds, military and non-military families, as well as learning abilities ranging from gifted to mild autism and students with extensive dyslexia. In this investigative journey, I explore the connection between student knowledge, critical and reflective thinking, and actual skill application by utilizing a variety of tools and best practices to engage student participation with meaningful and lasting results.