The External Thermal Insulation Composite System (ETICS) is a common cladding technology that is widely used thanks to its well-known advantages. Despite previous studies dealing with ETICS durability in real-building case studies or involving accelerated ageing tests in climatic chambers, little progress has been made in the knowledge of the long-term durability of the system. In order to realize optimized maintenance plans for this component, the durability of the whole system, and of the most-used insulating materials for the ETICS (i.e., cork, polyurethane, rock wool, glass wool, grey EPS, and fiberfill wood), has been investigated. Based on previous experiments on ageing cycles, different climatic chambers were used to accelerate performance decay by simulating natural outdoor exposure in order to assess different physical and thermal characteristics (thermal transmittance, decrement factor, time shift, water absorption, thermal resistance, and conductivity). Recorded trends show that materials with lower thermal conductivity exhibit lower performance decay, and vice versa. The durability of the ETICS with different insulating materials (as the only variable in the different samples) was evaluated in order to quantify service life and then correctly plan maintenance interventions. Life-cycle assessment must take into account service life and durability for each material of the system. A higher durability of insulating materials allows for the execution of less maintenance interventions, with the loss of less performance over time. This study shows the physical and thermal behavior of the ETICS during its service life, comparing the differences induced by the most-used insulating materials. As a result of accelerated ageing cycles, the analyzed ETICS reveals a low grade of decay and measured performances show little degradation; for thermal conductivity, differences between the measured and the declared conductivities by technical datasheet were observed.