This chapter uses the ReaL Earth System Science project as a metaphor for investigating the landscape of assessment in science education. This framing turns the focus of the five questions away from the Earth system and toward the system of education assessment. This chapter is as much an assessment of what to assess as it is of how to asses. The adage “What gets tested is what gets taught” highlights the intertwined nature of these processes. This metacognitive and meta-assessment approach brings forth questions that provide direction for educational leadership.