This study looks at the capital of Colombia, Bogotá’s mobility department, and how this institution is using the bicycle as a tool to brand the city. Bogotá has had a remarkable increase in bicycle ridership for several years, this duo to the city's implementation of bicycle lanes and politicians that have incorporated planning that favors this transport method. Even so, the city still has challenges in making bicycle transportation inclusive for everyone. Research suggests that to make a city more inclusive, it is important to understand the struggles and dilemmas within the current planning. This study examines questions such as: Which group or specific users are a dilemma when planning and developing Bogota as a bicycle city? Why is this group or user a challenge or dilemma in the planning? And: Does this group fit into the planner's vision of a cycling city? Through interviews with important stakeholders, academics, and bicycle representatives, the study identified Bicycle messengers as a dilemma. Some representatives of this group are also interviewed. Together with field observation, the theoretical framework, and the found data, this study analyzes the three-research question and answers why bicycle messengers are a dilemma for planners, as they pose a security risk. This finding is further discussed in the paper along with the theories of place branding, the right to the city, and a southern theory approach. Exploring the fact that the mobility department's own vision and branding can be one of the causes of finding this group to be a dilemma.