In 2017, the mathematics assessments that are part of the National Assessment of Educational Progress (NAEP) program underwent a transformation shifting the administration from paper-and-pencil formats to digitally-based assessments (DBA). This shift introduced new interactive item types that bring rich process data and tremendous opportunities to study the cognitive and behavioral processes that underlie test-takers’ performances in ways that are not otherwise possible with the response data alone. In this exploratory study, we investigated the problem-solving processes and strategies applied by the nation’s fourth and eighth graders by analyzing the process data collected during their interactions with two technology-enhanced drag-and-drop items (one item for each grade) included in the first digital operational administration of the NAEP’s mathematics assessments. Results from this research revealed how test-takers who achieved different levels of accuracy on the items engaged in various cognitive and metacognitive processes (e.g., in terms of their time allocation, answer change behaviors, and problem-solving strategies), providing insights into the common mathematical misconceptions that fourth- and eighth-grade students held and the steps where they may have struggled during their solution process. Implications of the findings for educational assessment design and limitations of this research are also discussed.