Digital learning environments are dynamic systems that require learning designers to leverage environmental conditions and the needs of their learners. While many frameworks and studies have explored pedagogical reasoning, little emphasis has been placed on the dynamic decision-making processes of learning designers. To advance the exploration of pedagogical reasoning and dynamic decision-making in digital learning environments, we proffer a conceptual framework that supports these practices through the promotion of reflection-in-action, external representations, and the use of conjecturing strategies to maneuver through the learning design space. Theoretical and practical implications are considered for how pedagogical reasoning and dynamic decision-making can be integrated into learning design curricula and educational policy.