This chapter sets out a framework for analyzing technology-rich assessment systems. The framework comprises several relevant aspects identified in the growing research literature related to digital assessment. In order to test all aspects of the framework, we use it to analyze three distinctive and innovative assessment systems: STEP (Seeing The Entire Picture) in Israel, SMART (Specific Mathematics Assessments that Reveal Thinking) in Australia and STACK (System for Teaching and Assessment using a Computer algebra Kernel) in the United Kingdom. By using the framework to analyze these three systems, their main characteristics are identified, and some differences between them are highlighted. The chapter ends with a reflection on the usefulness of the framework.