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Every organization, firm and company aims at becoming the best among its peer in the same industry. For this to happen, organizations, firms and companies come up with a plan known as a strategic plan. This is the plan that the organization, firm or company uses and implements so that it can gain an edge over its competitors. This strategic plan highlights some SMART (Specific Measurable Attainable Realistic and Time bound) goals that the organization, firm or company needs to focus on so as to realize its strategic plan. Similarly Kenya just like an organization has its strategic plan which is known as Vision 2030. Vision 2030 is a long-term development plan for the country. Like any other strategy, vision 2030 faces several constraints which derail its realization and the first step towards correcting this is to identify some of the factors that pose a threat to the success of the vision. This paper aims at bringing out the challenges that face a smooth implementation of vision 2030 and the Millennium Development Goals. The paper first highlight the pillars of Kenya vision 2030 and MDGs then goes ahead to identify several contemporary issues that negatively affect the attainmen