Current environmental crisis calls for sustainable solutions in the building industry. One of the possible solutions is to incorporate timber-framed constructions into designs. Among other benefits, these structures are well established in many countries, originating in traditional building systems. This paper focuses on experimental timber-frame walls. Different wall assemblies vary in thermal insulation materials and their combinations. We investigated ten experimental wall structures that have been exposed to natural external boundary conditions since 2015. The emphasis was on their state in terms of visual deterioration, mass moisture content, and thermal conductivity coefficient. We detected several issues, including defects caused by inappropriate realization, causing local moisture increase. Material settlement in loose-fill thermal insulation was another issue. Concerning was a significant change in the thermal conductivity of wood fiber insulation, where the current value almost doubled in one case compared to the design value determined by the producer.