The cross-Line-of-Control-trade is said to be the biggest confidence-building measure on Kashmir between India and Pakistan. Many analysts argue that it is a cosmetic step which was started by the two governments as they were compelled to address the humanitarian aspect of the Kashmir problem due to various factors. However, even if it is a cosmetic step, the question arises as to whether it has really benefitted the Kashmiri people in different spheres of their lives – economic, psychological, emotional, and political. The paper also tries to explore that despite the many problems that traders have to come across during their business dealings, Kashmiris are determined that this process is sustained and does not fall prey to the uncertain relationship that exists between India and Pakistan. The paper traces the events of the past 14 years that led to the initiation of this confidence-building measure (CBM), discussing in detail the benefits and problems that are being faced by the traders, and suggests a number of recommendations as a way forward.