Education is an important life process that plays a vital role in forming the foundation for a student’s future better being, as it equips learners with basic knowledge, skills and attitudes that will enable him/her to cope well in life. This study examined the factors that lead to increased school dropout among high school students in Kirinyaga County, with the aim of suggesting the possible solutions thus promoting learner’s retention among high schools. The objective of the study was to determine the factors leading to increased school dropout in Kirinyaga County. This study was undertaken in response to high school dropout rates and poor academic performance among the high school students in Kirinyaga County. In this study, questionnaires were used as data collecting instruments. Questionnaires were preferred because of their ability to ensure confidentiality to responses from respondents. A visit was done to 18 high schools, which are located in Kirinyaga, which will include both day and boarding.  Questionnaires were issued randomly to ensure fairness. 18 principals and 108 teachers. The entire questionnaire was returned hence equivalent to 100%. Responses received from questionnaires was organized, tabulated and analyzed using frequencies and percentages. Data was analyzed by use of Statistical Package for Social Sciences (SPSS). Findings were presented using frequency tables. This study established that low socio-economic status, poor school performance, drug and substance abuse, peer pressure among others contribute to student dropout. Poverty leading to financial problems was also cited as a cause of school dropout. The study recommends that the government should take stern measures against traders who employ children to pave way for these children to go to school. Similar studies should be done in the other counties so as to find a long lasting solution to the problem. Rampant uncontrolled pregnancies are an impediment to education and progress among teenagers. I therefore conducted this research to find out the major causes of these pregnancies and what really prompts them. Although the problem of teenage pregnancies is well understood in quantitative terms, there is scanty of evidence on the qualitative aspects.It presented the conceptual framework, detailing the linkage between the depended and independed variables. Field work data collection was conducted using key informant interviews and case stories. Data analysis was undertaken using qualitative techniques such as trend analysis.To my finding, the key causes of teenage pregnancies were identified as cultural practices, poor parenting, poverty and inadequate sex and family planning education.Culture as a people’s way of life is good. However, culture at times can lag behind with certain practices becoming repugnant to wellbeing, which in this case is about the education and career development of young girls. Particular practices came out as a root cause of teenage pregnancies in Narok south constituency and these are intaleng’o or emanyata and emurata. These are celebrations in Maasai land which brings people together to late nights.Poverty as evidenced by scarcity of basic needs leads to cases of teenage pregnancies. Exchange of sex for food, clothing and even gifts has led to most of the affected young girls to become pregnant.Lack of literacy and knowledge on sexuality are associated with early and often unprotected sexual debut. Family planning education is weak across the county as reported by one health worker I interviewedThis study sought to identify the root causes of teenage pregnancies in Narok South constituency. From the analysis, it is clear that socio-cultural factors such as traditional dances and ceremonies, poor parenting and cultural changes combine with the poverty situation to generate and perpetuate the problem. Girls who fall victims of teenage pregnancies end up facing stigma and discrimination and their access to education and career development is radically reduced.