This chapter explores the technological advancement of the Bulgarian economy in the era of digitalization, highlighting the transformative potential of emerging technologies such as artificial intelligence (AI), the Internet of Things (IoT), and big data analytics. It evaluates Bulgaria’s progress in digital infrastructure, innovation capacity, and integration into the global digital economy while benchmarking its performance against other EU countries. Despite improvements, Bulgaria faces persistent challenges, including low R&D investment, limited high-tech exports, and a significant digital skill gap. The chapter employs composite indicators like the EU Innovation Scoreboard (IUS) and Digital Economy and Society Index (DESI), alongside targeted measures such as R&D spending, patent applications, and broadband penetration, to provide a comprehensive analysis of Bulgaria’s technological landscape. It highlights structural weaknesses, including poor collaboration between academia and industry, underfunded research ecosystems, and insufficient SME digitalization. However, the chapter also identifies strengths in intellectual property assets and expanding ICT sectors. Bulgaria’s strategic frameworks, such as the Innovation Strategy for Smart Specialization and the Digital Transformation Strategy, are critically assessed for their role in fostering innovation and digitalization. The chapter concludes with policy recommendations to enhance R&D investment, improve digital skills, and strengthen public-private partnerships to drive sustainable technological growth.