Global change-type droughts will become more frequent in the future and threaten forest ecosystems around the globe. A large proportion of the Estonian forest sector is currently subject to artificial drainage, which could probably lead to negative feedbacks when water supply falls short because of high temperatures and low precipitation during future drought periods. In this short article, we propose a novel research perspective that could make use of already gathered data resources, such as remote sensing, climate data, tree-ring research, soil information and hydrological modelling. We conclude that, when applied in concert, such an assembled dataset has the potential to contribute to mitigation of negative climate change consequences for the Estonian forest sector. In particular, smart-drainage systems are currently a rare phenomenon in forestry, although their implementation into existing drainage systems could help maintain the critical soil water content during periods of drought, while properly fulfilling their main task of removing excess water during wet phases. We discuss this new research perspective in light of the current frame conditions of the Estonian forest sector and resolve some current lacks in knowledge and data resources which could help improve the concept in the future.