The role of HCI to support cyclists has been researched for many years. However, there has been relatively little work on the interaction with and acting within real-world traffic situations. We collaborated with professional cycling instructors to understand experiences of (novice) cyclists in complex real-world urban traffic situations and existing coaching and teaching strategies. Building on this understanding, we designed a system informed by these strategies: an on-the-bike Virtual Cycling Coach (VCC), a system aware of its user’s actions and context that delivers coaching interventions in appropriate moments. In a qualitative in-the-wild study with 25 participants we evaluated if the VCC – as Wizard-of-Oz prototype – can offer a coaching experience. Our findings show that the VCC enables processes such as reflection and learning comparable to conventional coaching settings. We discuss limitations and implications for similar designs in complex, highly context-dependent realms.