Assisted migration of forest tree populations through reforestation and restoration is a climate change adaptation strategy under consideration in many jurisdictions. Matching climates in which seed sources evolved with near future climates projected for plantation sites should help reduce maladaptation and increase plantation health and productivity. For threatened tree species, assisted migration outside of the species range could help avert extinction. Here, we examine lessons, limitations, and challenges of assisted migration through the lens of three assisted migration field trials of conifers in Canada and Mexico: Pinus albicaulis Engelm., an endangered subalpine tree species in the mountains of western North America; the Picea glauca (Moench) Voss × P. engelmannii Parry ex Engelm hybrid complex, of great economic and ecological importance in western Canada, and Abies religiosa (Kunth) Schltdl. & Cham., a tree species that provides overwintering sites for the monarch butterfly. We conclude that: (a) negative impacts of climate change on productivity of Picea glauca × P. engelmannii may be mitigated by planting seed sources from locations that are 3 °C mean coldest month temperature warmer than the plantation; (b) it is possible to establish Pinus albicaulis outside of its current natural distribution at sites that have climates that are within the species’ modelled historic climatic niche, although developing disease-resistant trees through selective breeding is a higher priority in the short term; (c) Abies religiosa performs well when moved 400 m upward in elevation and local shrubs (such as Baccharis conferta Kunth) are used as nurse plants; (d) new assisted migration field trials that contain populations from a wide range of climates tested in multiple disparate climates are needed, despite the costs; and (e) where naturalization of a migrated tree species in recipient ecosystem is viewed as undesirable, the invasive potential of the tree species should be assessed prior to large scale establishment, and stands should be monitored regularly following establishment.