Digitalization is transforming the tax landscape, reshaping the operations of tax departments, authorities, and professionals. With rapid digital advancement, there has been a shift toward real-time reporting, e-invoicing, and greater reliance on digital data. This change is driven by investments in data analytics, robotic process automation, cloud platforms, and, more recently, artificial intelligence in both corporate and public sector tax domains. Drawing on existing literature, OECD reports, and trade journals, this chapter explores the implications of emerging trends in tax technology, focusing on how digitalization is reshaping expertise across commodities, organizations, and tax professionals, and its impact on legitimacy in tax compliance and administration. It highlights critical issues arising from these trends and identifies key research questions for further exploration. This chapter proposes a research agenda focused on three key areas: professional, technical, and organizational. It encourages the exploration of the interaction between tax professionals and technology on their work, as well as the changes in organizational dynamics in order to understand the implications of tax technology on tax compliance and administrative practices. It also suggests investigating how tax technology is redefining tax work within organizations and the new competencies required by tax professionals to navigate and leverage technology in the digital era, while maintaining trust and legitimacy within the tax system.