An overview of testing and measurement in North America is provided, covering topics related to privacy laws and regulations, online proctoring, artificial intelligence, accommodations, accessibility, and the “opt out of testing” movement that are currently defining measurement in North America. This is not to say that these challenges are unique to North America; in fact, the challenges related to these topics are being faced all over the world in varying degrees and the same opportunities exist, but these topics are of particular importance when it comes to measurement and assessment in North America. Building on these observations, a discussion of how advances in technology and computing power provide an opportunity to challenge the status quo related to assessment; these advancements will allow assessment of skills in more authentic ways that will provide better insight into someone’s knowledge, skills, and abilities. The question we should be asking and attempting to answer is “How can assessment developers leverage the power of the cloud and technology to measure skills more accurately and create higher fidelity in the assessment process?”