Greenhouse technology has an important role to play in minimising adverse effects of climate variability on vegetable production. Studies indicate that greenhouse farmers face several challenges, sometimes leading to the abandonment of Greenhouses. The types and levels of severity of the challenges have not been adequately documented and acted upon on a context-specific basis, yet the demand for Greenhouse fresh produce is increasing, particularly in populated urban areas. This study identified and evaluated core challenges, available opportunities, and a concatenation of the challenges with productivity perceptions among Greenhouse farmers in Kericho County. A cross-sectional survey design drawing on data from 10% of Greenhouse farmers from each of the six Sub-counties was adopted for the study. Structured and unstructured interview schedules were administered to 59 sampled farmers and 16 Extension agents. The Henry Garret ranking method was used to analyse ranked data on challenges from farmers’ views and potential opportunities from Extension agents. A one-sample Wilcoxon test was used to analyse the deviation of views from ‘neutral’. Challenge due to pests and diseases was significantly higher than hypothesised median of 3 (neutral); Z = 5.198, P< .01. Cost of inputs and lack of finances for maintenance were significantly higher than neutral; Z = 5.061, P< .01 and Z = 3.810, P< .01 respectively. The top five challenges based on Garrett scores were pests & diseases, cost of inputs, maintenance costs, inadequate water, and initial costs. Top-ranked opportunities were integrated pest & disease management, farm-inputs subsidy, information on crop varieties, support from extension and capacity building in water harvesting. Concatenations existed between productivity of greenhouse units with quality of produce, ease of access to markets and profitability of greenhouses. The study recommends stakeholders’ concerted effort towards utilisation of the opportunities identified to enhance sustainable Greenhouse productivity among smallholder vegetable producers