Cover crops provide multiple benefits including nutrient management, erosion control, and soil improvement. Timely cover crop establishment is a primary challenge and a barrier to wider adoption. Cover cropping is particularly sensitive to growing season length and rainfall. Drilling the cover crop after harvest is the most consistent method. Broadcasting followed by shallow incorporation can also be successful, while broadcasting without incorporation gives the least satisfactory results. If there are insufficient growing degree days for cover crop establishment after harvest, cover crops can be interseeded or overseeded. Competition from the cash crop for light, water, and nutrients can compromise cover crop survival until cash crop harvest, while the limits of broadcast seeding apply as well. Research on cover crops worldwide is addressing many of these challenges, but more is needed on the best species and the optimum timing for these alternative seeding methods, especially as influenced by site-specific conditions.