This chapter projects the continuity and change in Singapore's defence planning shaped by strategic and technological 'disruptions' of the twenty-first century. It argues that Singapore's security constants, historical experience of vulnerability, lack of strategic depth and natural resources, and asymmetries in demography, have been augmented by three main disruptions: return of geopolitics and strategic competitions in the Indo-Pacific, diffusion of emerging technologies, and convergence of 'hybrid' security challenges, which undermine Singapore's conceptions of deterrence and defence. The second part outlines Singapore's changing defence planning approaches in the evolving context of Total Defence strategy, Ops-Tech collaborative defence innovation, strategic foresight, and operational requirements of the SAF. Lastly, the chapter projects military innovation trajectories of the Singapore Armed Forces (SAF), focusing on the 'Next-Gen' SAF 2040 transformation. Its technological patterns include digitisation, robotisation, and sensor revolution, signifying a shift towards 'automated' forms of warfare, while its organisational change stipulates a shift from adaptation to transformation, particularly with the establishment of the Digital and Intelligence Service, a fourth branch of the SAF on par with the Republic of Singapore Navy, Air Force, and Army. The contours of the SAF 2040, therefore, may signify a major military change for Singapore.