In the Midwest, it can be beneficial to interseed cover crops into corn (Zea mays L.) since there is a limited time for them to establish and grow after corn harvest. Research conducted in four environments in North Dakota quantified the impacts of planting method and time of planting when grown with or without corn competition on the establishment, and development of three cover crop species. Limited light intensity (less than 20%) under the corn canopy drastically reduced cover crop development. Soil water can also constrain cover crop establishment. Model simulations suggest soil water is more limiting for cover crop establishment in August compared with June or July. Interseeded cover crops had no effect on corn yield or the following soybean (Glycine max (L.) Merr.] crop due to minimal amounts of biomass produced.