As a nation, Kenya hopes to achieve Education for All (EFA) by the year 2015. This is an uphill task given the various challenges in the education sector. The year 2015 is also significant globally because it is the target year for the fulfillment of the eight-millennium goals. Kenya looks forward to have her people achieve the millennium goals together with other people worldwide. The pivotal hinge for these important target goals is education levels of the people involved and look forward to benefit from the fruits of EFA, millennium goals and industrialization. For such matters therefore, Kenya is trying her best to have her people educated. The secondary school segment in the education cycle of a Kenyan is important for three major reasons: a) It de-links one from elementary (primary) learning. b) It provides a chance for one to complete the cycle for basic education. c) It anchors as the springboard to either tertiary or higher learning. However, pandemic secondary school dropout in Kenya is alarming. For instance, in a period of ten years, 1992-2002, every secondary school cohort suffered not less than ten percent school dropout e.g. the highest dropout rate for the girls was fifty percent in the 1997/2000 cohort. The average dropout and completion rates for girls in the period under consideration were twenty percent and eighty percent respectively. For the boys they were fourteen percent and eighty-seven percent respectively. Some of the reasons that lead to the pandemic secondary school dropouts have been elucidated in this paper. They include poverty, early pregnancies/marriages, HIV/AIDS, drug-abuse and low-self esteem. Importantly, every secondary school dropout in Kenya signifies unfulfilled objective, goal, and aim for the individual as well as for the community at large. Emerging from this fact is perhaps a crucial question, where do the individuals who dropout of the learning cycle without basic education go? Alternatively, what do these persons do wherever they go? The most critical issue in this conundrum is perhaps the role of secondary school principals. In their endeavor to check dropout rates and concurrently enhance retention rates, they ought to change their managerial approaches to suit this twenty-first century that is apparently full of challenges to secondary school retention of students. In this article, the author discusses some of the approaches secondary school principals (managers) may use to alleviate dropout rates in Kenya. There is hope. (Contains 13 tables and 4 figures.)