The article presents experimental studies of typical Finnish highly insulated (HI) envelopes with thermal resistance values ( R value) for the wall and roof inside the ventilation cavity between 7.7 and 8.1 m2K/W and 13 m2K/W, respectively. The conditions in the ventilation cavities were studied by using typical and increased R values for the exterior part of the cavity, which were 0.18 m2K/W and 1.57 m2K/W in the walls, and 0.13 m2K/W and 2.13 m2K/W for the roof. With higher exterior R values of 1.57 m2K/W and 2.13 m2K/W, the cavity temperature increased only after closing the inlet gap of the cavities. If the cavity inlet was closed, the restriction of the outlet gap from 20–25 mm to 10 mm had no significant effect on the temperatures. A closed ventilation inlet resulted in increased absolute humidity in the cavity, which indicates that the restriction of cavity ventilation should be made with care to avoid impairing the drying-out ability. The computational analysis showed that the optimal air change rates in the wall and roof cavities of HI structures were 4–40 1/h and 20 1/h, respectively. The conventional 22-mm-thick wood cladding enables safe cavity conditions in HI walls if the vapor barrier is vapor tight and other moisture sources are low. A lower heat flux and additional heat loss caused by cloudless sky at night support the observation that HI roofs have a higher moisture risk. In HI roofs, a conventional exterior R value of 0.13 m2K/W should at least be increased to the range of 0.3–0.4 m2K/W, which is achieved, for example, by a 20-mm-thick mineral wool board under the roofing. The use of mold-resistant materials in the ventilation cavity is recommended to mitigate the possible ramifications of the moisture behavior of HI roofs.