This study examines digital factors affecting voluntary tax compliance among self-employed in Azerbaijan, an emerging economy undergoing rapid fiscal digitalization. Using Transaction Cost Theory, Technology Acceptance Model, and Behavioral Economics, an integrated model linking corporate digitalization, personalized notifications, and secure digital infrastructure is developed. Data from a 2024 survey of 410 taxpayers is analyzed via two-stage PLS-SEM. Results confirm all three factors significantly improve compliance, with personalized notifications having the strongest effect. The study highlights digital trust and suggests a compliance-by-design approach for fiscal sustainability.