The free primary education policy has led to a significant increase in primary school enrollment in the country, from 8.6 million children in 2008 to 9.9 million in 2012. Increased enrollment complicated the work of teachers in the classrooms in the wake of FPE. This article seeks to document the challenges that teachers face in Kenyan classrooms across six urban sites in Kenya. Data come from the Education Research Program at the African Population and Health Research Center, collected in the months of January to March 2012. This article presents data from Focus Group Discussions, which were analyzed using thematic qualitative analysis. Results show that teachers across the six urban sites faced numerous challenges, with the most striking one being the process of evaluation by district quality assurance officers, who need to take into consideration the circumstances in which teachers teach in the schools across the country. Overall, the study called for the need to take the contexts of the respective schools into consideration even as they visit schools to ensure that teachers adhere to the quality assurance and standards procedures. This is because different schools have different teachers implementing the curricula.