Mechanization has significantly advanced various sectors, particularly agriculture, by enhancing productivity, efficiency, and sustainability. But still mechanization finds challenges in several agricultural systems. This study explores the challenges of mechanization in some distinct agricultural systems in India. Through survey of previous literature from India, various agricultural systems were identified. Following, brainstorming on such agricultural systems, based on ranking, distinct agricultural systems with significant mechanization challenges were selected and insights were made. Results states the practices such as the water logged paddy farming system, protected cultivation, pandhal system, hill farming, mixed and intercropping systems, organic farming, and shifting cultivation were identified as distinct agricultural systems holding unique hurdles towards mechanization. Each system was discussed with the insights derived on brainstorming. Practicable strategies to overcome the discussed hurdles on the distinct systems were identified and presented in short. In overall, the study explores the various research gaps and challenges upon mechanization of some agricultural systems in India for which further investigations and actions needed.