Assessment methodologies such as BREEAM and LEED allocate points based on prescribed interventions that promote design features or strategies considered to be more sustainable than others. A focus on accumulating numerical scores, however, often fails to address pertinent contextual issues, particularly within developing countries. This paper examines the use of four assessment systems in Kenya—two international systems, LEED-US and Green Star SA-Kenya; and two locally developed systems, Green Mark Kenya and the Safari Green Building Index. The paper compares the relative weighting of different categories under each system, and assesses their appropriateness to a Kenyan context, with reference to the suitability of active technology versus passive design approaches. The paper examines selected examples of ‘green’ buildings in Nairobi, reflecting on the influence of different methods of assessment on the adopted design approaches. The paper argues that international rating systems, such as LEED, often focus on a Western construct of sustainability featuring a systematic bias towards global rather than local perspectives, with an emphasis on physical environmental factors. In pursuit of objectivity, the measurement of non-contextual parameters untailored to local circumstances (e.g., energy performance) is prioritised at the expense of those contingent on local conditions or climate.