This paper investigates the effect of employing different display design principles for human–machine interaction in helicopters. Two obstacle avoidance support displays are evaluated during low-altitude forward flight. A baseline head-up display is complemented either by a conventional advisory display or a constraint-based display inspired by ecological interface design. The latter design philosophy has only been sparsely applied in the helicopter domain. Twelve helicopter pilots participated in an experiment in a research flight simulator. We found no significant effects of the displays on objective performance measures. However, there was a trend of decreasing pilot workload and increasing situation awareness when employing the support displays, as compared to the baseline display. The constraint-based display had the largest positive effect and increased the resilience of the pilot–vehicle system toward unexpected events when considering the safety of the flown trajectories. Pilots preferred the advisory display in nominal situations and the constraint-based display in off-nominal situations, reproducing similar findings from research in the fixed-wing domain. This experiment showed the potential of the developed constraint-based display to improve subjective pilot ratings, pilot preference, and safety during unexpected events. Future research will investigate more complex scenarios with longer time frames, possibly eliciting more divergent effects of different display design principles.