Tomato is among the promising commodities in horticultural production in Kenya. Over the years, tomato production in Kenya has intensified. Yields, however, continue to remain low due to a myriad of constraints. This paper describes production practices and identifies challenges and opportunities for increased tomato productivity in smallholder production in Kenya. The study uses plant health clinics as primary providers of data. Association between variables is tested using multinomial logistic regression, and Goodness-of-fit test used to examine how well the model fits the data. In addition, ANOVA and Student’s t-test were used to compare group means. Smallholder tomato production in Kenya is characterised by a decline in the area under tomato cultivation. Furthermore, production is dominated by male farmers while participation by youth is minimal. Coupled with these, a diverse range of biotic constraints impede tomato production, and for their management, use of conventional synthetic pesticides is the preferred practice by farmers. The findings of this study underscore the need to increase women and youth participation in tomato production. In addition, there is a need to explore initiatives that enable farmers to access available technologies such as improved seed. For the management of biotic constraints, smallholder farmers should be encouraged to consider alternatives other than an overreliance in the use of synthetic pesticides.