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District heating systems are central to Europe’s decarbonisation strategy and its 2050 climate-neutrality objective. However, district heating is deeply embedded in the socio-economic system and the built environment. This makes compliance with policy targets at the local level particularly challenging. The issues are attributable to two factors. Firstly, the process is characterised by a high degree of complexity and multidimensionality. Secondly, there is a scarcity of local resources (e.g., land, surface waters, waste heat, etc.). In Bucharest, Romania, the largest district heating system in the European Union, the process of decarbonisation represents a particularly complex challenge. The system is characterised by large physical dimensions, high technical wear, heavy dependence on natural gas, significant heat losses and complex governance structures. This paper presents a strategic planning exercise for aligning the Bucharest system with the Energy Efficiency Directive 2023/1791. Drawing on system data, investment modelling, and local resource mapping from the LIFE22-CET-SET_HEAT project, the study evaluates scenarios for 2028 and 2035 that shift heat generation from natural gas to renewable, waste heat, and high-efficiency sources. The central objective is the identification of opportunities and issues. Options include large-scale heat pumps, waste-to-energy, geothermal and solar heat. Heat demand profiles and electricity price dynamics are used to evaluate economic feasibility and operational flexibility. The findings show that the decarbonisation heat supply in Bucharest is technically possible, but financial viability hinges on phased investments, interinstitutional coordination, regulatory reforms and access to EU funding. The study concludes with recommendations for staged implementation, coordinated governance and socio-economic measures to safeguard heat affordability and system reliability.