Terrain access is a critical factor influencing the feasibility of forest operations in steep mountainous terrain. Long extraction distances coupled with terrain obstacles can favor the use of helicopters in timber extraction in such areas. However, helicopter logging in the Italian Alps is not commonplace when compared to other Alpine regions, for example, in Switzerland and Austria. The use of light-lift helicopters has recently caught the attention of practitioners as an alternative to more traditional medium- to heavy-lift aircraft in the Alps. This article reports the findings of two preliminary case studies using light-lift helicopters for the extraction of high value timber and fire-damaged timber subsequently exposed to bark beetle disturbance. In order to provide a comprehensive analysis of the factors affecting helicopter logging productivity, the two case studies were separately analyzed using time-element analysis supported by on-board global navigation satellite system (GNSS) devices. Additionally, an external video camera was used to continuously monitor the operations. The payload utilization was 86% for the extraction of high value timber and 70% for fire-damaged timber subsequently exposed to bark beetle disturbance. Variation in the turn time was mostly related to the hooking, choker return, and load times, as well as flying distance. Above all, the load hooking time explains c. 27% of the variance, revealing its critical influence on logging productivity.