In recent years, India and Singapore have developed a strong bilateral security and economic partnership that has assumed a central position in India's strategic engagement in Southeast Asia. Having sought strategic engagement with India for many decades, Singapore has now successfully positioned itself as India's leading political partner and economic gateway to the region. At the same time, India and Singapore have actively pursued close defence ties, including frequent joint training and the assumption of an active maritime security role by India in Southeast Asia. The recent decision by India to allow the Singapore air force and army to operate long term training facilities on Indian territory represents a significant development in Indian strategic practice and may presage a more permanent Indian security presence in East Asia. This article will examine these developments and consider to what extent the emergent security relationship between India and Singapore should be seen as a desire to balance China's growing economic and political dominance of the region and to what extent it reflects a 'natural' strategic sphere for India stretching from Aden to Singapore and beyond into East Asia.