This paper will etch out the changing optics that have characterized interaction between Afghanistan and the Indian subcontinent from the late nineteenth century to contemporary times. Particular emphasis will be laid on teasing out the imprint that the rise, expansion, consolidation and subsequent retreat of the British empire in the Indian subcontinent left on the shaping of the geo-political dynamics between New Delhi, Rawalpindi and Kabul. It will be argued that the strategies of imperial control and expansion came to strongly underpin the dynamics of interaction between them. It will be argued that an engagement with historical processes is of seminal significance in providing us a sound empirical rubric for contextualizing policy choices made by these three state actors.