The central objective of this study was to identify major issues and dilemmas in intelligence gathering and sharing as a counterterrorism strategy. The research covered diverse categories of informants from various institutions and agencies cross cut by intelligence gathering and sharing in Kenya. These included: security officers from the national police service, members of civil society organizations working in areas of security and human rights, academicians and members of the public. Government officers, members of community policing department and former police reservists were also included. Exploratory research design was applied. Based on the design, a historical interrogation approach was applied to interrogate various facets of IG & S and terrorism in Kenya whereby they were chronologically documented, and the changes that have occurred over time analyzed. Data analysis was done through mixed analysis method. The study found out that diverse security reforms that have been implemented in the country since independence which have helped to improve IG & S. Major improvements were highlighted to have been streamlined in technology used, training and the information shared. Among the different forms of intelligence, human intelligence and signals intelligence were found to have played the greatest role in containing TT. The study concluded that the question of intelligence being effective or ineffective in curbing transnational terrorism is dependent on the reaction of all security agencies who receive it. The study recommended that the ability of terrorists to morph should be met with equal efforts by security forces changing their strategies in gathering and sharing information on terrorism from members of the public. All agencies should continuously go through retooling and capacity building on early warnings. Furthermore, there is need for interagency cooperation in sharing intelligence. Both domestic and foreign agencies involved in intelligence sharing should work together to boost their confidence with each other to enhance their readiness and commitment to share security intelligence.