Perennial Lewis flax (Linum lewisii Pursh) has the potential to be grown as a new oilseed crop that could simultaneously meet commodity production, ecosystem service provisioning, and farm resiliency goals. Despite many potential benefits, Lewis flax remains minimally explored as an agronomic crop. Determining agronomic best practices for producing economically relevant stands of Lewis flax is critical to its adoption as an oilseed crop. Several aspects of Lewis flax agronomic production were explored through the lens of adaptive management between 2020 and 2022. Initial field trials aimed at assessing spring-seeded Lewis flax row spacing, plant population density, and intercropping strategies with legumes and grasses failed due to poor establishment. Heavy rains and excessive weed pressure further complicated attempts to reestablish these initial trials. We established additional Lewis flax plots via fall and dormant seeding in response to the failure of our first experiment. This second experiment focused on exploring row spacing, population density, and seeding timing impacts on flax production. Flax yield did not differ among our treatments, averaging 59 kg ha−1. The low yields realized by our field trials may be due to several factors including need for harvest technology optimization, high weed pressure, and need for Lewis flax genetic improvement. Our study is a first step toward developing recommendations for optimal production strategies for Lewis flax in an agronomic context. Continued exploration of methods to improve management and yield of Lewis flax will be critical to its successful development as an agronomic crop.