The rapid development of information and communication technologies has profoundly transformed mathematics education worldwide, with dynamic software such as GeoGebra and Desmos enabling visualization, interaction, and automated verification of mathematical concepts. At the same time, the rise of automated solvers and artificial intelligence (AI) introduces both opportunities and critical risks. AI-based systems offer adaptive learning, step-by-step reasoning, and real-time feedback, yet raise concerns about equity, assessment integrity, and student autonomy. This paper analyzes the Serbian experience tracing the progression from dynamic mathematics software toward AI-supported learning environment. In the Republic of Serbia, the COVID-19 pandemic accelerated the integration of dynamic mathematics software, introducing new approaches to teaching and teachers’ professional development. Through case studies from primary and secondary schools, it is illustrated how digital tools enhance students’ engagement, conceptual understanding, and independent problem-solving. Recommendations are offered for teacher training, curriculum integration, equity of access, research, and collaboration, while taking care of the essential aims of mathematics education, which are the reasoning, creativity, and critical thinking.