Over the past 80 years an unresolved issue in rain-fed crop-pasture rotations by scientists and farm advisors has been whether to recommend sowing a perennial pasture either alone or with a cereal cover crop. Researchers and agronomists have typically advocated sowing pastures alone to improve pasture productivity, but a large proportion of farmers continue to sow pastures under a cover crop suggesting a perceived financial advantage with the latter establishment method. Whether there is a real financial benefit of establishing pastures under a cover crop presents a practical Farm Financial Risk problem. Our study is based on four years of field experiment results (2008 to 2012) along a 200 km transect running north and south of Wagga Wagga, New South Wales, Australia. Analysis of these results with information on local weather and price variations using “The Intensive Farming (IF) model” (Hutchings et al, 2016), suggests the following: (1) sowing the pasture alone is a more reliable method of establishing lucerne (Medicago sativa L.) pasture than sowing under a cover-crop; and (2) the additional costs of sowing a lucerne pasture alone are met in the majority of years by its increased productivity compared with pastures sown with cover-crops. Comparing median decadal cash balance values for pastures with stocking rates of 10, 15 and 20 dse/ha, our results show an advantage with direct-sowing for farms with high equity. Farms with low equity may not be helped by agronomic improvements, but find it best to focus on reducing debts.