BACKGROUND: Planners and politicians in many countries seek to increase the proportion of trips made by cycling. However, this is often challenging. In England, a national target to double cycling by 2025 is likely to be missed: between 2001 and 2011 the proportion of commutes made by cycling barely grew. One important contributory factor is continued low investment in cycling infrastructure, by comparison to European leaders. METHODS: This paper examines barriers to cycling investment, considering that these need to be better understood to understand failures to increase cycling level. It is based on qualitative data from an online survey of over 400 stakeholders, alongside seven in-depth interviews. RESULTS: Many respondents reported that change continues to be blocked by chronic barriers including a lack of funding and leadership. Participants provided insights into how challenges develop along the life of a scheme. In authorities with little consideration given to cycling provision, media and public opposition were not reported as a major issue. However, where planning and implementation have begun, this can change quickly; although examples were given of schemes successfully proceeding, despite this. The research points to a growing gap between authorities that have overcome key challenges, and those that have not.