After completing his conscription (compulsory military service) as a Rifleman in a Light Infantry Regiment, Kuperwasser was commissioned as an Officer in the Artillery Corps in 1976, in a position in which he was a Forward Observer embedded with frontline Infantry, Special Forces and Armoured Corps teams during the 1978 South Lebanon conflict and the 1982 Lebanon War. During his stint as a young officer in the Artillery, he also completed a licensed course on flying observer Helicopters and was for a time an "Air Observer" i.e a helicopter pilot spotting targets for the Artillery. In 1985 he became a Battery Commander of a Self-Propelled Artillery unit. In 1987 he was seconded to the Military Intelligence Directorate, in which he served in many different capacities. For two-years, beginning in 1992, he was the Assistant Defense Attache for Intelligence at the Israeli Embassy in Washington, D.C.. Four years later, Kuperwasser became an Intelligence Officer at the IDF's Central Command for three years. Following this position, Kuperwasser immediately assumed the role as Head of the Analysis and Production Division of the IDF Directorate of Military Intelligence. According to his profile IDC Herzliya's International Institute for Counter-Terrorism, during his time in this role "He has a significant role in determining Israel's coping methods with terror as well as regional developments, and sharing such analysis with the US and other foreign entities."