This study assessed the success or failure of plan implementation in Kenya by investigating the extent to which planned estimates for educational projects were actually attained. Using six sets of five-year national development plans, we calculated an implementation ratio for each program showing actual expenditure as a ratio of planned expenditure. Our results indicated that out of the 78 implementation cases examined, there were 73 cases of overspending, and only five, of balanced spending, an indication of 93.3% implementation failure rate. We concluded that there is a persistent and substantial shortfall in the attainment of plan targets, a situation that calls for restructuring of the entire planning process.