A previous study on the encroachment of North American northern red oak Quercus rubra L. into the mesic Scots pine forest (in central Poland) revealed high abundances of seedlings and saplings under shrubs, with lower abundances in open areas or clumps of bilberry Vaccinium myrtillus L. It was unclear whether the regeneration success of Q. rubra is enhanced by the presence of shrubs due to their “nurse effect”, and how burying acorns of different sizes in soil or moss affects the survival of oak seeds and seedlings (a “burial effect”). Results of a previous observational study were verified in an experimental study: a pool of 900 large‐, medium‐, and small‐sized acorns was sown under moss cover in open areas and within bilberry clumps and in soil under shrubs in 2018 and monitored for 3 years in natural conditions. The majority of sown acorns were lost, mainly due to acorn pilferage, lack of germination and the death of sprouting acorns. However, acorn and seedling survival depended significantly on acorn size and differed among the microsites studied. Viable seedlings were twice as likely to develop from large‐ and medium‐sized as from small‐sized acorns, and they grew mainly from acorns sown under moss cover, confirming a positive “burial effect.” Seedling survival was three times higher in bilberry and open areas, than under shrubs; however, seedlings “nursed” by shrubs were less threatened by large ungulates. Only a small part of the pool of sown acorns contributes to the reproductive success of Q. rubra in the mesic Scots pine forest. Microsites characteristic to this type of forest are suitable for northern red oak regeneration; however, bilberry favors acorn survival and germination and early seedling growth, moss cover favors acorn survival and germination, while shrubs protect surviving seedlings from herbivory.