The purpose of this study was to establish the challenges facing Nairobi City County Government in the implementation of devolution strategy. The study adopted a case study research design since it was focusing on the Nairobi City County alone. The study used both primary and secondary data. The respondents of the study included the 10 county executive committee members of the County who are in charge of the various departments at the County level. Primary data was collected through an interview guide. The interview guide was validated using content analysis where the draft was availed to two of the respondents for their critique and input. A final draft was finally made to be used for data collection. The data collected was analyzed using content analysis. The study findings reveal that the main challenges that face the implementation of the devolution strategy by the Nairobi City County include the physical and political environment; the national government and its agencies whose actions at times contradict actions taken by the Nairobi City County government; inadequacy of resources both financial and human capital and resistance from both the Members of City County Assembly, employees, the electorate and the business community. It was confirmed that the Nairobi City County has the capacity to successfully implement the devolution strategy subject to a number of requirements being met. The study revealed that if the Nairobi City County gets access to adequate resources, then the question of capacity to implement the devolution strategy will not arise. Currently the capacity to implement the devolution strategy is affected by the scarcity of resources both financial and human. The possible solutions to the challenges include more funding by the national government or seeking alternative means of raising revenue by the Nairobi City County government. Stakeholder involvement at all levels of implementation will also assist in reducing resistance. Another possible solution is to educate the members of the County Assembly on the need to separate politics and development issues in order to enable them understand the reasons why their support for implementation of the devolution strategy is significant. The study recommends the Nairobi City County to seek homegrown solutions to the challenges facing implementation of its devolution strategy. Development of policies concerning devolution should carefully consider reviewing the roles of the central government so that conflict of interest can be eliminated. There should be clear policies governing the implementation of devolution strategy in order to avoid confusion. Currently the existing policies need to be streamlined to provide the Nairobi City County government with enough capacity to implement the devolution strategy successfully