Background: Commercial trucker health is a vital public health concern. Enhanced understanding of the multiplicity, diversity, interdependence, and complexity of policies, resources, and stakeholders relevant to healthful living in trucking worksites can guide future interventions. Purpose: This article examines how the environmental attributes of commercial trucking worksites influence truck drivers' opportunities for healthful eating and active living and provides a preliminary discussion on how complexity science can help design more efficacious interventions. Methods: A 250-item audit instrument was used to measure the presence of corporate, social, and built environment attributes of 25 diverse trucking worksites that can influence food choices and physical activity of truckers. Results: Findings from truckstops, trucking terminals, warehouses, and highway rest areas along key transportation routes revealed that these worksites are severely burdened by structural and institutional barriers and essentially represent what can be called "healthy living deserts." Discussion: Comprehensive interventions to address organizational barriers for health-supportive trucking worksites are critical because truck driver health has far-reaching ramifications for drivers and others. Translation to Health Education Practice: Because traditional worksite wellness programs for truckers have had limited success, the application of complex systems methodologies has an increased potential to advance high-leverage, sustainable intervention configurations.