A monitoring system can tell us that something has changed. But an engineer needs to know something more fundamental: what does that change mean for the asset? When observations are connected to their physical location, component, monitoring purpose, operating conditions, related measurements, inspections, interventions, and history, data becomes more than an isolated signal—it becomes engineering context. The article explores why structural monitoring needs to move beyond datasets and dashboards toward systems that understand the physical assets they observe. It looks at how context can help distinguish genuine structural behaviour from sensor or operational effects, how conflicting evidence should be presented without creating false certainty, and why the right context depends on the decision an engineer needs to make. It also considers how automation can reduce the manual effort of connecting measurements, drawings, inspection records, operating conditions, and asset history, allowing engineers to focus less on reconstructing context and more on interpreting evidence and making informed decisions.