Learners are the key stakeholders of a school for it to be registered by the Department of Education. However the retention of these learners in Kenya's Secondary Level Education is a great challenge in Kenya. Every secondary school dropout signifies unfulfilled objective, goal and aim for the individual as well as the community at large. The purpose of the study was to establish the factors affecting subsidized free day secondary education (SFDSE) in enhancing learners' retention in secondary schools in Kenya. The study was guided by the following specific objectives: to determine the effects of adequacy of school finances and teaching/learning resources in enhancing learners' retention in secondary schools in Kenya. The target population of the study comprised of 3,993 stakeholders in the education sector in Bungoma County, Kenya. A sample size of 340 respondents was selected purposively for the study. Cross-sectional survey research and proportional stratified sampling were adopted to obtain the Educational Officers, Principals, B.O.G chairpersons, P.T.A chairpersons and Parents from each Sub County in Bungoma County. Questionnaires and interview schedules were used to collect data from the respondents. Qualitative data collected was analyzed using content analysis while quantitative data analyzed using descriptive statistics. The results indicated that enrollment and transition rates of learners had increased since the introduction of SFDSE by the government in the year 2008. The study also revealed there is an acute shortage of teachers despite the expansion of various secondary schools in Bungoma County to three streams per class. The study recommends that the Government employees more teachers to meet the international standards of teacher students ratio in schools.T