The article explores the concept of digital empathy as an innovative tool for managing the emotional intelligence of a region’s brand in the context of the digital transformation of territorial marketing and the transition to an impression economy. The fundamental shift in the paradigm of territorial branding from static visual identity to dynamic management of emotional resonance with key stakeholders of the territory is substantiated. A comprehensive architectural model of using Big Data and artificial intelligence technologies to collect, analyze and interpret the emotional patterns of the target audiences of tourists, investors, residents and the business community is revealed. The author’s four-stage methodology for the formation and correction of the emotional intelligence of a region based on predictive analytics, tonality analysis, computer vision and generative AI is proposed, including emotional audit of the territory, segmentation of audiences by psychographic characteristics, personalization of communications and continuous crisis monitoring in real time. Practical cases of the introduction of digital empathy technologies in three key areas of regional management are considered in detail: tourism and the hospitality industry, investment marketing and the formation of a comfortable urban environment. Special attention is paid to the ethical challenges and risks associated with algorithmic manipulation, the threat to privacy, the Sinister Valley effect and the protection of personal data, as well as the principles of “ethical digital empathy” as a necessary condition for the sustainable development of territories. Recommendations are given on the transformation of the organizational culture of regional authorities and the change of the KPI system to integrate metrics of emotional well-being into the practice of public administration. The results of the research can be used by regional and municipal government bodies, marketing agencies, specialists in the field of territorial branding and digital development of territories.