The tripartite partnership between the National Institute of Education, Academy of Singapore Teachers, and schools provides the contextual and structural enablers to create a model of situated professional learning in Singapore. Situated professional learning creates authentic learning experiences for teachers that are contextualised to everyday practice. There are deliberate attempts to create a theory–practice nexus and understanding that relates to authentic classroom settings. Despite its strengths, the situated professional learning model also has its challenges. Depending on the teachers’ profiles and mindsets, the value and challenges for professional learning may vary. This chapter takes a reflective lens to elaborate on the positive attributes of situated professional learning as well as its challenges and makes recommendations as opportunities for value-adding the model.