Various theories and models discuss how instructional designers can develop systems that allow learners to engage in problem-solving. To date, many of these theories and models that guide design often describe how learners engage in meaning-making within a situated context; however, they do not address strategies instructional designers can use to coordinate contextual factors impacting the environment. While these perspectives provide a more authentic view of action, they often overlook the design decision-making processes to support learning that occur within these situated environments. This makes it challenging to design learning systems that support complex interactions. Although studies have begun to emerge focusing on instructional design decisions, there is a need for a framework to guide how instructional designers engage in decision-making while designing for situated, real-world experiences. We then offer a theoretical design framework to facilitate design decision-making by conjecturing within a bounded rationality, exploring through analogical reasoning, and designing-in-action.