This article examines the fundamental measurement gap between out-of-home (OOH) advertising and performance-driven digital channels. While OOH continues to rely on probabilistic attribution models such as store visit tracking, web lift studies, and geographic correlation analysis, native and push advertising were built with measurement as a native capability. The article challenges the industry's "honest measurement" narrative, arguing that deterministic tracking, direct attribution paths, and competitive intelligence tools give native and push advertisers a structural advantage that OOH cannot replicate. It also explores why marketers continue to romanticize billboards despite these limitations and explains how prestige, visibility, and brand perception often influence media decisions more than measurable business outcomes.