Ultra-early seeding of spring wheat (Triticum aestivum L.) on the northern Great Plains can increase grain yield and grain yield stability compared to current spring wheat planting systems. Field trials were conducted in western Canada from 2015 to 2018 to evaluate the impact of optimal agronomic management on grain yield, quality, and stability in ultra-early wheat seeding systems. Four planting times initiated by soil temperature triggers were evaluated. The earliest planting was triggered when soils reached 0–2.5 °C at a 5 cm depth, with the subsequent three plantings completed at 2.5 °C intervals up to soil temperatures of 10 °C. Two spring wheat lines were seeded at each planting date at two seeding depths (2.5 and 5 cm), and two seeding rates (200 and 400 seeds m−2). The greatest grain yield and stability occurred from combinations of the earliest seeding dates, high seeding rate, and shallow seeding depth; wheat line did not influence grain yield. Grain protein content was greater at later seeding dates; however, the greater grain yield at earlier seeding dates resulted in more protein production per unit area. Despite extreme ambient air temperatures below 0 °C after planting, plant survival was not reduced at the earliest seeding dates. Planting wheat as soon as feasible after soil temperatures reach 0 °C, and prior to soils reaching 7.5–10 °C, at an optimal seeding rate and shallow seeding depth increased grain yield and stability compared to current seeding practices. Adopting ultra-early wheat seeding systems on the northern Great Plains will lead to additional grain yield benefits as climate change continues to increase annual average growing season temperatures.