Artificial hollows are commonly used to mitigate the scarcity of den and nest sites that threatens fauna species globally, but there is a risk that these do not provide suitable microclimates for the populations they are intended to support. We monitored temperature, humidity and occupancy in artificial dens (nest boxes and chainsaw-carved cavities) provided for the critically endangered Leadbeater’s possum (Gymnobelideus leadbeateri) in south-eastern Australian forests. Monitoring occurred over both winter and summer in five habitat types spanning a broad elevational gradient (110–1580 m asl). We then used a biophysical model to explore the physiological consequences of the den temperatures recorded, and the potential effectiveness of behavioural strategies in reducing thermoregulatory costs. Monitoring revealed that nest box temperatures tracked ambient over both seasons, ranging from −5.5°C to 48.5°C, while chainsaw hollows provided more stable internal conditions. However, we found that inferences regarding the thermal suitability of artificial dens were site-specific, and dependent upon habitat type, season and assumptions around behavioural strategies. During winter, behaviours such as the construction of large, insulative nests and huddling are likely critical in overcoming high energy costs associated with poorly insulated artificial dens. In contrast, during summer high thermoregulatory costs were predicted for the warmest (lowland) site and coincided with low nest box occupancy. Our study reinforces the importance of factoring in local climates, and behavioural and physiological strategies employed by target taxa, when implementing artificial den programs to support fauna populations.