For decades, we’ve measured structures with increasing precision—yet understanding them has remained elusive. From point-in-time inspections through non-destructive testing to today’s data-rich structural health monitoring systems, the industry has expanded its toolkit without fully rethinking the questions behind it. The result is a paradox: more data, but not necessarily more insight. In this conversation with Prof. Anjan Dutta, we explore the gap between measurement and meaning—why monitoring often stops at documentation, and what it takes to move toward true interpretation. At the heart of this shift is a new perspective: structures are not static assets to be inspected, but dynamic systems whose behavior unfolds over time. Bridging that gap is where Structural Intelligence begins.