Community Engagement is a buzz term used by academics, International development Organizations and planning and development practitioners. All RFPs, TORs and Technical proposals make mention of having community engagement in the development of the plans. Experience shows that it makes for a good technical proposal etc., but is it just rhetoric? Can community engagement be effectively achieved as outlined in the literature? In recent times in Trinidad and Tobago the issue of community engagement made international headlines as there was protest action taken over the start of construction of a controversial section of a highway. Some were angered as they highlighted that their voices and concerns were not being heard and addressed. What are the factors affecting effective community engagement in Trinidad and Tobago? To answer the question the case study of Waterhole was used as it is a microcosm of community engagement issues in Trinidad and Tobago. This paper identifies theoretical and practical approaches to community engagement in land use planning and compares them with the practice in the case study Waterhole. On site interviews were done with the residents of the Waterhole Community as well as officials from the Land Settlement Agency in order to collect the data to answer the question posed. It was found that, amongst others, ethnicity, power distances, violence, attitude of the state, limited budgets affect community engagement in Trinidad and Tobago. Suggestions for addressing these and other issues are highlighted.