Tax non-compliance amongst small businesses is an ongoing concern for governments globally and typically linked to deliberate tax avoidance or tax evasion. However, insights into understandings of this issue are scarce. Accordingly, this study explores factors contributing to tax non-compliance amongst small businesses. Observations and interviews with small business owners who were tax non-compliant, as well as small business owners who were tax compliant reveal several issues. Findings show that the non-compliant group faced socioeconomic disadvantages and were vulnerable at the core. They often suffered complex and compounding factors including internal factors (demographic disadvantages, situational and psychological problems, low capability), and external factors (complexity of the tax environment and lacking intermediary support). As such, their tax non-compliance was not a deliberate choice of avoidance, but rather an accumulation of factors creating tax apprehension and making compliance challenging. Findings also highlight the necessity of providing more guidance regarding ethical conduct of tax agents and promoting understanding and a compassionate approach from the tax office and tax agents when working with this at-risk clientele. The study suggests a comprehensive view of self-efficacy from both internal and external dimensions and its role in tax apprehension. The findings provoke reconsideration by tax researchers and tax authorities regarding the underlying factors of tax non-compliance within small businesses, and how it might constructively be addressed.