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Durand Line is considered to be the first ladder for souring relations between Pakistan and Afghanistan and today it has become the most important border due to war on terror as NATO forces are not authorized to cross it while it has never barred tribes living on both sides of the border and ruminants of the Al-Qaeda and the Taliban. During 19th century, settling territorial boundaries, British marked this line as formal border between BritishIndia and Afghanistan, Afghanistan shares its border with six countries but much treacherous border is with Pakistan. Unfortunately, Afghan ruling elite did not accept independence of Pakistan and raised boundary issue. This led to the bitter relations between two neighbors, while India provoked and backed conspiracies about Pukhtunistan issue, a territorial claim of Kabul. Today the issue in question is the different opinions whether this treaty has expired after passing of 100 years or not. Incidents of violence and terrorism have increased due to porous border since American led war on terror. The deployment of international troops to Afghanistan once again gave this old bilateral issue a significant international dimension and led to a political paradox. In the recent past, the Canadian Government offered to resolve the issue of cross border drug trafficking, terrorism; immigration etc between Pakistan and Afghanistan and for that very purpose, Dubai Process has been initiated. This paper aims at discussing the historical facts related to the cross border issues, its impacts on the relations between both countries, the efforts of Canadian government, its follow-up and its future implications for the south Asian region