Against a backdrop of three decades of interest in the institutional development of learners’ holistic competencies, countries in Asia have increasingly incorporated twenty-first century skills into their educational goals. The path from policy to practice has not been seamless. This is in large part due to a lack of awareness of the magnitude of the shift that integration of such skills requires for education provision. In this chapter, “big picture” and “audit-observation” examples of exploring alignment within education systems are discussed to highlight the need to consider the multiple factors in play for implementation of the shift. The challenges being experienced worldwide in the adoption of twenty-first century skills prompt questioning as to whether the architecture of our current education systems is adequate to achieve twenty-first century learning goals.