The territory has remained a bone of contention between modern nation states. Pakistan and Afghanistan have also no exception from it. Pak-Afghan relations have been in turmoil since the day when Afghanistan refused to accept Pakistan as a country and voted against its newly independent neighbor in the United Nations. It all happened in lieu of that Afghanistan is of the view that the North-Western Frontier Province (NWFP), currently known as Khyber Pakhtunkhwa (KPK), Baluchistan and some areas of Punjab are the parts of Afghan territory. Afghanistan breached all the previous agreements made over the Durand Line calling it just an imaginary line. Based on this entire scenario, this research study analyzes the changing dynamics of Pak-Afghan relationships in different eras driven by different factors. It discusses the pre-colonial impacts on the relationship between the two countries, it also probes what happened right after 1947 and then highlights the impacts of 9/11 tragic events. Reviewing the existing literature and the opinions of different political scientists on this issue, this study discusses the historical background of Pak-Afghan borderland. Moreover, it also attempts to shed light upon the geostrategic importance of Pakistan and Afghanistan in the region so that the political decisions on the persisting issue are made in a way that they favor the interests of both the states. This paper also elucidates the literature available on the colonial legacy of the Durand Line.