As foresters struggle to engage private forest landowners with sustainable forestry practices, research highlights the value of amenities and nontimber goods and services to landowners. With the value landowners place on this range of “cultural ecosystem services” (CES) and the demonstrated ability of CES to drive individual forest management decisions, we use a participant observation approach in east-central Illinois to examine practitioner opportunities to better address landowners' CES goals. Results illustrate the bundle of CES that landowners enjoy and illustrate a range of compatibility and conflict landowners perceive between active forest management and enjoyment of CES. Based on a preliminary framework derived from the literature to make forestry more compatible with landowners' CES values, we identify practitioner uncertainties and research avenues to better address four specific CES considerations: aesthetics management, natural resource interpretation, recreation considerations, and land legacy.