This study investigates the barriers faced by cities in their efforts to increase the number of urban cyclists and aims to identify best practices to fulfil cities' ambitions. The research explores the multi-dimensional nature of the obstacles and highlights the significance of understanding and addressing them effectively. By examining bike policies, sustainable mobility programs, existing literature, and conducting interviews with experts, this study provides insights into the common themes that prevent cities from achieving their goals. The findings contribute to the development of best practices that can support cities in their ambition to increase urban cycling.This study is a multi-case study, where the study compares the city Malmö and The Hague. The Hague is a leading example for bicycle use, while Malmö strives to become a bicycle-friendly city. The methodology employed in this research includes several components: a literature review to explore barriers and enablers of urban cycling, a theoretical analysis, a comprehensive review of bike policies and sustainable mobility documents in both cities and interviews to delve deeper into recurring themes identified in the document analysis. The discussion section integrates the literature review, theory, and results, highlighting the best practices for promoting urban cycling.In this study, the theory of path dependency is employed, which refers to a process where initial moves lead to further moves in the same direction, limiting future choices. It involves three phases: Preformation, Formation, and Lock-in. Additionally, the theoretical framework incorporates the three factors of path dependence identified by Low et al. (2005). These factors are relevant to the study because they relate to urban planning and active transport. The three factors are: technical, institutional, and discursive. Overall, understanding path dependency and its factors (technical, institutional, and discursive) enables more effective strategies in urban planning and active transportation to overcome barriers and promote sustainable cities.Through an analysis of previous research, theory, and results it becomes evident that the establishment of a support base and the implementation of a combination of hard and soft measures play a crucial role in fulfilling cities' bike ambitions. The support base requires diverse stakeholders to understand and support bike policies. Effective communication help engage stakeholders and expand support. Overplanning with various options enhances policy resilience. Striking a balance between hard and soft measures is crucial for increasing urban cyclists. Hard measures like infrastructure development are initially important, but a balanced approach ensures an effective strategy.By adopting these best practices, cities can successfully increase the number of urban cyclists. However, it is important to emphasize that achieving this ambition goes beyond formulating a policy; it requires the establishment of a support base and a balanced approach that incorporates both hard and soft measures. This study provides cities with insights into potential barriers and enablers, offering guidance for examining their specific urban contexts and working towards their cycling goals.