Context drives learning design, but too often context is not considered within learning design literature. Reported skill gaps lead to considerations around learning design and the security, completeness and depth of learning developed by learning designers in adult learning. Frequently learning is linked to context, where learning environments are often described as complex. However, rarely do studies consider disorder, created by a lack of consideration for multiple contexts or learning domains (simple, complicated, complex and chaotic) and their governing principles. We draw upon literature from the fields of learning theory, complexity theory and risk governance to illuminate this challenge, suggesting that a lack of security, completeness and depth of knowledge attainment could impact the fitness of learners entering uncertain labour markets. After signposting gaps in existing thinking, we introduce a direct content analysis of a systematic review, comprised of 384 aspects of literature from the fields of pedagogy and andragogy, to demonstrate a lack of conscious consideration for the multiple learning contexts that exist in adult learning design. This gap illustrates an opportunity for learning designers in the field of adult learning to improve the depth, completeness and security of learning experiences. To this end, we present a new Learning Awareness Framework as a feedback mechanism to guide learning design. Our approach is distinctive in the way we link literature in the field of learning to complexity theory and risk governance, where our perspective appears to be unique to the field of adult learning. Finally, our recommendations for a Learning Awareness Framework to guide learning design according to multiple contexts seem to be the first of its kind.