During August-September 2012, an outbreak of Foot-and-mouth Disease (FMD) due to serotype Southern African Territories-2 (SAT2) occurred on a large, extensively grazed dairy farm in Nakuru County, Kenya. Over 29 days, 400/644 (62.1%) cattle were recorded as displaying clinical signs consistent with FMD. Out of the 18 management groups present, 17 had clinical cases (weighted mean incidence rate 3.5 per 100 cattle-days, 95% CI 2.4, 5.1; range 0.064-10.9). Transmission may have been encouraged when an infected group was moved to a designated isolation paddock. A four to five day minimum incubation period was apparent in five groups for which a point source exposure was evident. Further transmission was associated with the movement of individual animals incubating infection, use of a common dip and milking parlour, and grazing of susceptible groups in paddocks neighbouring to infectious cases. Animals over 18 months old appeared to be at highest risk of disease possibly due to milder clinical signs seen among younger animals resulting in reduced transmission or cases not being recorded. Cows with a breeding pedigree containing a greater proportion of zebu appeared to be at lower risk of disease. The outbreak occurred despite regular vaccination (three times per year) last performed approximately three months before the index case. Incidence risk by the lifetime number of doses received indicated limited or no vaccine effectiveness against clinical disease. Reasons for poor vaccine effectiveness are discussed with antigenic diversity of the SAT2 serotype and poor match between the field and vaccine strain as a likely explanation. Detailed field-derived epidemiological data based on individual animals are rarely presented in the literature for FMD, particularly in East-Africa and with the SAT2 serotype. This study provides a detailed account and therefore provides a greater understanding of FMD outbreaks in this setting. Additionally, this is the first study to provide field-derived evidence of poor vaccine effectiveness using a SAT2 vaccine. Further field-based measures of vaccine effectiveness in line with evaluation of human vaccines are needed to inform FMD control policy which has previously relied heavily upon experimental data and anecdotal experience.