ABSTRACT Highway sign support structures are critical components of transportation infrastructure, particularly within the Connecticut Department of Transportation (CTDOT) bridge management system. Ensuring their structural integrity through regular inspection and maintenance is essential for public safety and cost-effective asset management. This study presents a comprehensive investigation combining non-destructive field testing and finite element modeling (FEM) to assess the performance and longevity of a cantilever-type highway sign support. In collaboration with CTDOT, a full-scale field test was conducted on a selected sign support structure using advanced instrumentation, including strain gauges, accelerometers, and anemometers, to monitor real-time responses to environmental loads over a six-month period. The collected data was used to calibrate and validate a detailed three-dimensional FEM developed. The model accurately replicated the structural behavior observed in the field, with predicted strain values within 10% of experimental results. Analysis revealed that the structure experienced only 22.4% of its elastic yield capacity under peak loading conditions, indicating substantial remaining strength. Furthermore, the study explored the effects of fatigue loading, demonstrating its significant impact on long-term performance. These findings suggest that the current 34-year service life assumption may be conservative, and with proper monitoring and maintenance, sign support structures could remain functional well beyond this threshold, offering potential cost savings and improved asset management strategies.