Singapore is experiencing a growing number of people with illnesses requiring chronic care, particularly individuals with multiple and complex conditions. However, increasing the capacity and capabilities of the primary care workforce to suit the needs of the evolving population is not entirely straightforward in Singapore and involves multiple interrelated issues. To more explicitly approach the issue of whether and how to enhance primary care services in Singapore, we convened a 2-day meeting, termed the Primary Care Roundtable, comprising 50 local and international stakeholders and experts with an interest in primary care delivery. Private general practitioners, polyclinics, hospitals, ministries, and academic researchers were represented. The goal of the meeting was to: (1) surface the range of issues facing Singapore in addressing the challenges of providing excellent chronic care; and (2) develop a “qualitative causal model” of the issues raised. The qualitative causal model represented the group’s hypotheses regarding how key system features promoted or inhibited improving primary care, and facilitated identifying leverage points for maximizing positive change. In this paper, we summarize the status of this work, and discuss how the dynamic framework developed by the participants can serve as a “boundary object” to facilitate further discussion among stakeholders, and as foundation for research and policy action.