In Siberia, most boreal forests are located in an area with relatively moist forest soils, which makes logging activities possible exclusively during the frost period with a permanent snow cover and stable sub-zero temperatures. As the global climate is experiencing a trend towards warming, it is reasonable to suppose that the duration of the logging season might shorten over time, influencing the economic potential of Siberian forests. To test this hypothesis, we created a concept for calculating the duration of the logging season, taking into account the economic and climatic peculiarities of doing forest business in these territories. Using the long-run daily-observed climatic data, we calculated the duration of the logging season for eight representative stations in Krasnoyarsk Krai (Yeniseysk, Boguchany, Achinsk, and Minusinsk) and Irkutsk Oblast (Bratsk, Kirensk, Tulun, and Yerbogachen) in 1966–2018. We found strong evidence of logging season duration shortening for almost all considered stations, with an uneven effect on the start and end boundaries of the season. Climate warming has almost no effect on the start date of the season in winter, but it significantly shifts the boundaries of the season end in spring. Using the autoregressive-integrated-moving average modeling (ARIMA) models, we demonstrated that, in the near future, the trends of the gradual shortening of the logging season will hold for the most part of the considered stations. The most pronounced effect is observed for the Achinsk station, where the logging season will shorten from $148.4\pm 17.3$ days during the historical sample (1966–2018) to $136.2\pm 30$ days in 2028, which reflects global warming trend patterns. From an economic perspective, a shorter duration of the logging season means fewer wood stocks available for cutting, which would impact the ability of companies to enact their logging plans and lead them to suffer losses in the future. To avoid losses, Siberian forest firms will have to adapt to these changes by redefining their economic strategies in terms of intensifying logging operations.