Seed dispersal is key to forest regeneration and often depends on the behavior of seed scatter-hoarding animals. However, our understanding of the decision-making of scatter-hoarders and how vegetation structure at different spatial scales affects dispersal patterns remains limited. We studied seed dispersal at the forest edge across multiple spatial scales (habitat, sub-habitat, microsites) between and within habitats with distinct vegetation structure. Our model system is a mixed-oak forest dominated by holm oak (Quercus ilex) and an adjacent shrubland dominated by the shrub Retama sphaerocarpa. For three years, we tracked the movement of acorns by a keystone scatter-hoarder, the Eurasian jay (Garrulus glandarius). At the coarse scale, jays did not show a preference for caching acorns either in the forest or in the shrubland when the source tree was within the forest. However, when the source tree was on the forest edge or was an isolated oak tree in the shrubland at < 200 m from the forest, jays showed a preference for caching in the forest. Conversely, when isolated oak trees were > 200 m from the forest, all acorns were dispersed in the shrubland. Dispersal distances were shorter within the forest than within the shrubland. At an intermediate scale, within the shrubland jays preferred to cache acorns under large retamas while avoiding gaps. In the forest, jays also avoided gaps and preferred certain woody species and vertical vegetation structures, although these preferences varied across feeders. At the finest scale, jays selected stones as cache microsites. Thus, the selection of acorn caching sites followed a hierarchical and selective top-down process across different spatial scales. The position of the source trees in the landscape determined habitat preference and dispersal distance. We detected different preferences in response to similar vegetation structure and composition, indicating that the decision-making process is flexible at an intermediate scale that generates diverse spatial patterns of dispersal. This study sheds light on the intricate decision-making process of seed caching by scatter-hoarders, and the consequences for the spatial patterns of seed dispersal as well as the expansion and regeneration of oak forests.