Consulting forester business practices are challenged by significant decreases in the sizes of private forest properties and the changes in landowner values that accompany forestland parcelization. Though researchers have discussed the potential ways entrepreneurial foresters could adapt to these new ownership patterns and landscape dynamics, actual responses by foresters working in parcelizing landscapes are largely undocumented. We conducted twenty in-depth interviews with foresters working in New York State to determine (1) how foresters have experienced parcelization of properties they work with, (2) what challenges are associated with forestry projects on decreasing property sizes, and (3) what kinds of changes foresters are making to adapt to decreasing property sizes. We found that foresters across the state observe decreasing sizes of forest properties and see values of forest owners shifting beyond timber production, although most do not consider these changes to be the most urgent challenges to sustainable forestry and profitable forest consulting. Professional foresters are reacting to parcelization in diverse ways; while some are trying entrepreneurial approaches to reach new clients or offer different services, others are primarily interested in maintaining their traditional practices and roles. These findings indicate that strictly relying on independent entrepreneurial responses by private foresters may not be sufficient to close the gap between the historical role of consulting foresters and the trajectory of modern forest parcels. Additional measures like specialized training and policy changes may also be required to address the management challenges associated with forestland parcelization.