Accurate web measurement is critical for understanding and improving security and privacy online. Such measurements implicitly assume that automated crawls generalize to typical web user experience. But anecdotal evidence suggests the web behaves differently when seen via well-known measurement endpoints or measurement automation frameworks, for various reasons. Our work improves the state of web privacy and security by investigating how key measurements differ when using naive crawling tool defaults vs. careful attempts to match “real” users across the Tranco top 25k web domains. We find web privacy and security measurements significantly affected by vantage point and browser configuration. We conclude that unless researchers ensure their web measurement tools match real world user experience, the research community is likely missing important signals systematically. For example, we find browser configuration alone causing shifts in 19% of known ad and tracking domains encountered and altering the loading frequency of up to 10% of distinct JavaScript code units executed. We find network vantage point having similar, though less dramatic, effects on the same web metrics. To ensure reproducibility, we carefully document our methodology and publish both our code and collected data.