The purpose of this study is to discuss historical context of confidence building measures (CBMS) between India and Pakistan before 1999. This article delves into the development of CBMs from the post-partition era until the Kargil conflict in 1999, examining the significant initiatives, obstacles, and circumstances that influenced the process of building trust between India and Pakistan. Following the division, the two nations were involved in several conflicts, which greatly impacted their trust and cooperation. However, instances of diplomatic progress resulted in notable milestones, including the Tashkent agreement, the Simla agreement, and the Lahore declaration (1999). These initiatives primarily concentrated on enhancing military transparency, establishing communication channels (such as the hotline between military commanders), and fostering personal connections between individuals. Despite facing challenges such as political instability, terrorism, and mistrust, the pre-1999 CBMs provided a foundation for future discussions and stability.