BACKGROUND: Specialized drug shops (SDSs) are popular in Sub-Saharan Africa because they provide convenient access to medicines. There is increasing interest in how policymakers can work with them, but little knowledge on how their operation relates to regulatory frameworks. This study sought to describe characteristics and predictors of regulatory practices among SDSs in Kenya. METHODS: The regulatory framework governing the Kenya pharmaceutical sector was mapped, and a list of regulations selected for inclusion in a survey questionnaire. An SDS census was conducted, and survey data collected from 213 SDSs from two districts in Western Kenya. RESULTS: The majority of SDSs did not comply with regulations, with only 12% having a refrigerator and 22% having a separate dispensing area for instance. Additionally, less than half had at least one staff with pharmacy qualification (46%), with less than a third of all interviewed operators knowing the name of the law governing pharmacy.Regulatory infringement was more common among SDSs in rural locations; those that did not have staff with pharmacy qualifications; and those whose operator did not know the name of the pharmacy law. Compliance was not significantly associated with the frequency of inspections, with over 80% of both rural and urban SDSs reporting an inspection in the past year. CONCLUSION: While compliance was low overall, it was particularly poor among SDSs operating in rural locations, and those that did not have staff with pharmacy qualification. This suggested the need for policy to introduce levels of practice in recognition of the variations in resource availability. Under such a system, rural SDSs operating in low-resource setting, and selling a limited range of medicines, may be exempted from certain regulatory requirements, as long as their scope of practice is limited to certain essential services only. Future research should also explore why regulatory compliance is poor despite regular inspections.