In the context of climate change and the increasing ecological importance of pedunculate oak (Quercus robur L.) in European forests, sustainable regeneration strategies are essential for ensuring long-term forest resilience. This study investigates how different conditions of regeneration sites, namely areas under pine canopies, gaps (openings within the pine stand), inter-gap area (open zone surrounding the pine gaps), and clear-cut area (zone where trees were completely removed), affect the early growth performance of artificially regenerated oak stands in Central Europe. Seedling height, root collar diameter, sturdiness quotient (SQ), and light availability (via hemispherical photography) were assessed. The most favorable growth occurred in gaps and under-canopy sites, where light intensity ranged from 44% to 57%, and seedlings reached mean heights of 148.7 cm and 143.4 cm, respectively. In contrast, seedlings in clear-cut and inter-gap areas exhibited lower growth and higher SQ values, suggesting lower seedling stability. In these areas, the average seedling height was 127.2 cm in clear-cut opening and 137.9 cm in inter-gap area. These sites also had the highest light intensity, amounting to 100% and 89.85% of total incident radiation, respectively. Growth performance was also affected by cardinal direction, except within gaps. This study highlights the importance of microsite selection in oak regeneration and demonstrates how optimizing light conditions can enhance reforestation success and climate resilience. These findings contribute to sustainable forest management practices aimed at supporting adaptive strategies in temperate ecosystems facing climate change.