This study evaluates the effects of season and the length of service of chainsaw operators on the ability to achieve felling guidelines based on Occupational Health and Safety Regulations. The study consisted of measurements of stump cuts on three tree felling plots in two seasons: winter (in the presence of snow cover) and spring. In total, 90 stumps, 30 in each plot, were measured. Plots were similar in species composition, age, and forest habitat type, while variability in the study resulted from the age and occupational experience of saw operators. In addition, escape routes were assessed to evaluate whether they were in accordance with forest management Occupational Health and Safety Regulations. Season had no effect on stump attributes except for stump height, for which there was a significantly greater number of excessively high stumps in winter than in spring. More experienced saw operators were more competent in making precision saw cuts (e.g., depth of the notch cut, width of the hinge) and made fewer errors than a less experienced worker. In contrast, all escape routes prepared by a less experienced saw operator were prepared correctly, while about 8% of the escape routes prepared by longer−serving workers were incorrect. Since the preparation of escape routes depends only on compliance with Occupational Health and Safety Regulations and does not require special professional expertise, incorrect escape routes prepared by longer−serving saw operators probably reflect a disregard for risks caused by not following prescribed safety protocols.