This paper argues that Singapore’s foreign policy in Indonesia has been flawed because of its unevenness in engaging all the stakeholders who collectively formulate Indonesia’s security policy. Drawing from a novel conceptual framework initially developed to analyse Russian foreign policy, it notes the importance of foreign policy stakeholders, such as civilian elites and the general public. As demonstrated by underutilised empirical sources, such as parliamentary speeches and press releases, Singapore has not granted these groups substantial regard. There are several reasons for this poor engagement: Singapore’s ambivalent approach towards democratic solidarity and its suspicion towards Indonesian-led regionalism. Nonetheless, this behaviour has negatively affected the security relationship between the two states. The paper concludes that Singapore’s foreign policy must change to effectively engage with the changing political landscape of post-Suharto Indonesia.