Insurance sector contributes to the growth of the economy in addition to providing risk distribution avenue to asset owners. Whereas it is mandatory in Kenya, for all public service vehicles to have an insurance policy, at least third-party cover, many insurance firms in Kenya have shied away from providing insurance cover to public service vehicles plying for hire (commonly referred to as matatus). This has left only three insurance firms representing (6%) of all insurance firms registered in underwriting insurance for this growing class of motor vehicles. This study sought to identify the determinants of the uptake of insurance underwriting of public service vehicles plying for hire in Kenya. The specific research objectives were, to establish the extent to which the government regulations and reforms affect the uptake of insurance underwriting on public service vehicles plying for hire, to determine the influence of insurance industry practice on uptake of insurance underwriting on public service vehicles plying for hire and lastly, to establish the influence of shareholders’ interests on uptake of insurance underwriting on public service vehicles plying for hire in Kenya. The study adopted a cross sectional research design with a target population of thirty-eight insurance firms underwriting general insurance in Kenya. Primary data was collected by use of questionnaire having structured and open-ended questions addressed to business development managers or their equivalents in each of the insurance firms. Data was analysed using both descriptive and inferential statistics by use of R software and results presented in form of bar charts and frequency tables. The study findings reveal that the main insurance industry factors that affect uptake of matatu underwriting are usage of the vehicle, vehicle sitting capacity, type of cover and level of fraud in the industry. With regard to government regulations and reforms, stringent traffic rules and mandatory third party are the most frivolous factors that are considered when offering insurance to matatus. Relating to shareholders’ interests, the mandatory third-party cover and the risk-taking nature of the shareholders are the most critical considerations when insuring matatus. Lastly, in order to increase the number of insurers that underwrite matatus, the study recommends implementation of a centralized motor insurance data system, tighter anti-fraud systems, and strong internal controls in the insurance firms by the insurance regulator with the aid of the government. Areas of further study include comparative studies in other countries which have similar transport system as in Kenya