Energy efficiency renovation of building stock is an essential aspect of the climate change mitigation strategies in many countries. A large proportion of building stock is historical buildings. For this building stock, developing technology for safe internal insulation of external walls is crucial, preventing possible moisture damage to the building structures. Internal insulation is a risky technique as it has a high impact on the hygrothermal behavior of the wall. This study assesses the hygrothermal performance of massive masonry walls with 17 interior insulation systems exposed to different external boundary conditions, including a steady-state cycle, dynamic dry cycle, wind-driven cycle, and drying cycle. During the steady state cycle, the highest increase of moisture was observed under capillary active materials ranging from 39 to 119% increase in absolute moisture, with the exception of cellulose with an increase of only 7%. All the vapor-tight insulation systems showed no increase in absolute moisture during the steady-state cycle, with the exception being mineral wool in combination with a vapor barrier that showed a 30% increase in ablute humidity. In addition, relative moisture changes in masonry were measured. Results show that tested insulation systems exhibit similar thermal performance while having different moisture performance. Vapor-tight and vapor-open insulation systems exhibit different hygrothermal behavior under various test cycles depending on material vapor diffusion resistance. Numerical simulations are sensitive to the hygrothermal properties of materials.