Sport coaching is increasingly acknowledged as a stressful activity, especially for those coaching in community contexts. This highlights the significant need to identify the diverse sources of key stressors. The aim of this research was to explore the recurrent stressors experienced by novice coaches to better inform their coping strategies and reduce the dropout rate caused by stress. The novelty of this research lies in its longitudinal exploration of the daily hassles experienced by community sport coaches within their coaching role. Ontologically and epistemologically positioned within the interpretivist paradigm, we interviewed eight recently qualified cycling coaches over an 18-month period. Reflective thematic analysis developed three themes highlighting sources of stress over time: at the start of their participation, coaches discussed the hassles of accessing facilities and struggling to fit in; toward the end of their participation, coaches discussed feeling isolated. Results from this study can better inform the education and support delivered by national governing bodies of sport across the community and club landscape and increase sport psychology practitioners’ awareness of the daily hassles experienced by coaches.