This dissertation examines the role of taxation in shaping businesses’ sustainability across three dimensions: tax compliance, environmental taxation, and anti-tax avoidance regulation. Taxes serve as essential policy tools, influencing corporate behavior through revenue generation, redistribution, and regulatory incentives. In Chapter Two, a randomized field experiment in Bulgaria demonstrates how deterrence and moral appeal messages improve small firms’ payroll tax compliance, increasing fiscal sustainability. Chapter Three explores the impact of environmental diesel taxes on European trucking companies, revealing that while higher taxes reduce traffic, they also induce detours, leading to unintended environmental consequences. Chapter Four investigates the effectiveness of the EU’s Controlled Foreign Company (CFC) rules in curbing multinational tax avoidance, showing partial success but also evidence of regulatory circumvention. The findings underscore the potential and limitations of tax policies in promoting sustainable business practices, providing empirical insights for policymakers aiming to align taxation with sustainability goals.
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