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(1) Background: This paper proposes a strategy coupling Demand Response Program with Dynamic Thermal Rating to ensure a transformer reserve for the load connection. This solution is an alternative to expensive grid reinforcements. (2) Methods: The proposed methodology firstly considers the N-1 mode under strict assumptions on load and ambient temperature and then identifies critical periods of the year when transformer constraints are violated. For each critical period, the integrated management/sizing problem is solved in YALMIP to find the minimal Demand Response needed to ensure a load connection. However, due to the nonlinear thermal model of transformers, the optimization problem becomes intractable at long periods. To overcome this problem, a validated piece-wise linearization is applied here. (3) Results: It is possible to increase reserve margins significantly compared to conventional approaches. These high reserve margins could be achieved for relatively small Demand Response volumes. For instance, a reserve margin of 75% (of transformer nominal rating) can be ensured if only 1% of the annual energy is curtailed. Moreover, the maximal amplitude of Demand Response (in kW) should be activated only 2–3 h during a year. (4) Conclusions: Improvements for combining Demand Response with Dynamic Thermal Rating are suggested. Results could be used to develop consumer connection agreements with variable network access