In the majority of Kenya's arid regions, the predominant agricultural practice is subsistence farming. This study sought to examine the obstacles impeding the achievement of sustainable food security in arid regions by exploring potential strategies for advancing commercial agriculture. The study aimed to (i) examine opportunities for transforming subsistence agriculture in drylands, (ii) identify obstacles encumbering stakeholder efforts to achieve commercial agriculture in these regions, and (iii) ascertain strategic solutions for enhancing agricultural production, diversity, and capitalising on existing markets. The study was conducted in Turkana with reference to Marsabit, Samburu, and West Pokot counties in Kenya. It included 200 enterprising farmers and 40 government and development partners, picked randomly and purposely, respectively. The research employed a survey design utilising semi-structured questionnaires as the instruments for data collection. The study findings indicate that the subsistence nature of crop and livestock farming, inadequate research and technology, the absence of centralised meteorological and early warning systems, inefficient market development and access, and weak relationships between supply and demand in agricultural market systems are pivotal factors obstructing the transition of agriculture in drylands from a traditional economy to market-orientated systems. The study recommends educating local residents on the drawbacks of subsistence farming and offering alternatives for transitioning to commercial agriculture. It also advocates for the development of research and knowledge frameworks to incentivise local farmers, entrepreneurs, and policy organisations to commercialise crop and livestock farming, as well as encouraging all agricultural stakeholders to engage with Early Warning Systems and facilitate their coordination. Furthermore, dryland agroecologies must be enhanced to optimise available production resources through innovative agricultural practices and to improve farmers' market access by ensuring quality, quantity, efficient agribusiness frameworks, competitive product pricing, and consistent stakeholder engagement. The study suggests that anticipatory actions and durable solutions are prospective areas for future research to leverage and up-scale agriculture in the arid regions of Kenya.