The year 2022 marked the 30th anniversary of diplomatic ties between India and ASEAN and its progression into a comprehensive strategic partnership. Meanwhile, the unfolding geopolitical developments in the form of great power competition are fast eroding ASEAN’s centrality, thereby shrinking the diplomatic space that ASEAN needs to balance the two big powers (Zhiqun Citation2024). Amid increasing great power competition, ASEAN’s act of straddling between the US-led security guarantee and the economic benefits of engaging with China is becoming increasingly difficult (Thompson Citation2024). This shift in the geopolitical environment in Southeast Asia is also pressurising India to recalibrate its regional strategies. A historical analysis of Indo-ASEAN relations is necessary for situating the evolving dynamics between the two in the Indo-Pacific context, as past choices and constraints continue to shape Indo-ASEAN engagement. This Commentary analyses three major geopolitical factors involving India and ASEAN from India’s independence to the Indo-Pacific era. The factors are: the similarity in their geopolitical objectives, the degree of convergence in their geopolitical alignment with the United States (US) and China, and the relative power dynamics between India and ASEAN. Drawing on this analysis, the Commentary highlights the extent of strategic convergence between India and ASEAN during each period, showing how Indo-ASEAN relations have evolved from symbolic diplomacy to substantive strategic cooperation.