Tax compliance issues among self-employed business owners in Tanzania arise from complex and inequitable tax models, exacerbated by inconsistent enforcement and poor policy communication. This study investigates the dynamics of tax collection models in Tanzania, focusing on the perceptions of self-employed business owners across key regions, including Tanga, Dodoma, Arusha, and Mbeya. Drawing on findings from the TAPACO research project, the research employs a mixed-methods approach grounded in pragmatism a philosophy that emphasizes practical solutions. The sample size consists of 150 participants, with data gathered through structured questionnaires and semi-structured interviews representing various sectors within these regions. Entrepreneurial theories such as the Entrepreneurial Orientation (EO) Theory, Resource-Based View (RBV), and Theory of Entrepreneurial Alertness are utilized to frame the analysis of how self-employed business owners perceive tax estimates, bylaws, policies, the regulatory framework, and the tax collection environment. EO Theory explores how entrepreneurs’ risk-taking behaviors and reactivity to changes in the tax environment influence compliance decisions, The RBV examines how entrepreneurs strategically utilize their resources, particularly in making decisions about tax payments and investments in compliance technologies like Electronic Fiscal Devices (EFDs). The findings indicate that self-employed business owners in Tanzania face significant challenges with tax compliance, driven by inaccuracies in tax assessments, corruption within tax enforcement agencies, and a lack of training and infrastructure for adopting Electronic Fiscal Devices (EFDs). These factors, combined with poor communication of tax policies and regulations, have resulted in widespread non-compliance. The study concludes that effective tax compliance strategies must consider the entrepreneurial behaviors influenced by resource availability, risk tolerance, and alertness to regulatory changes. The study recommends strengthening anti-corruption frameworks within tax enforcement agencies, including regular audits, ethical training for task force members, and protections for whistleblowers. Transparency in tax collection operations is essential for rebuilding trust and encouraging voluntary compliance.