This article analyzes the innovative legal framework of Diia City in Ukraine, designed to foster technological ecosystem growth and attract international investment. The study evaluates its impact on residents and identifies challenges within the current legal system. The hypothesis posits that Diia City, with its preferential tax policies and streamlined regulations, could become a global benchmark for tech ecosystems. Legal stability and regulatory predictability are highlighted as critical for its success. A comparative methodology examines taxation structures and regulations affecting individual entrepreneurs (FOPs) and gig contracts. The hypothesis is verified through case studies and assessments of IT solutions in Ukraine. The analysis includes a literature review and examination of legal acts, offering a comprehensive evaluation of the reform’s innovations and benefits, with potential applicability to other European countries. Findings suggest Diia City shows promise as a global model but faces challenges affecting legal certainty. While regulations aim to protect both employees and employers, further evaluation is needed, especially amid war and economic fluctuations. This article provides insight into legal stability’s role in fostering innovation and contributes to the debate on legislative reforms influencing the labor market and Ukraine’s technological development.