Dryland wheat producers in Eastern Colorado incorporate fallow periods into their crop rotations to conserve soil moisture and stabilize yields, but increasing cropping intensity by reducing fallow frequency may improve profitability. Producers in this region often rely on fixed rotations that include fallow every second or third year; however, these rotations do not align fallow timing with information available before planting, such as moisture availability or weather forecasts. This raises the question of whether using preseason information to define threshold-based triggers for replacing fallow with a crop could outperform fixed rotations under dryland conditions. We compared fixed 2-year (wheat-fallow) and 3-year (wheat-millet-fallow) rotations to threshold-based flex rotations at field and farm scales using long-term crop experiment data (1994–2017) from the USDA-ARS Central Great Plains Research Station near Akron, CO. We found that flex rotations can outperform fixed rotations in annualized net returns, but the results are sensitive to the choice of information set, threshold level, and planning horizon. Overall, threshold-based flex rotations can support producers’ fallow management decisions by allowing them to condition cropping intensity on preseason conditions rather than on fixed rotation sequencing. Last, the findings point to a role for extension and policy interventions in improving producers' access to and effective use of the preseason information needed to implement flex-crop decisions.