Modern theories in educational assessment are rapidly transforming testing from unaccommodating ranking measures into flexible and informative tools that can be used to address the compelling needs of various stakeholders in education. The presentation will start with a brief introduction to smart learning, including some of the trending movements, such as individualized learning and MOOCs. Then, we will discuss how some of the cutting-edge smart testing technologies, such as Computerized Adaptive Testing and Cognitive Diagnostic Measurement, can facilitate smart learning. Our focus will be on how to build a reliable, and also affordable, web-based diagnostic tool for schools to classify students' mastery levels for any given set of cognitive skills that students need to succeed. In addition, we will show how Computerized Adaptive Testing can be employed to support individualized learning on a mass scale.