Student assessment plays a vital and growing role in primary and secondary education today. The days of laboriously handwriting test answers in little blue books to be interpreted by graders are drawing to a close. Measuring how well students and districts are performing relative to state educational standards is now accomplished through online, technology-based testing. High stakes summative testing involves simultaneously assessing large groups of students within a district or school system. Formative testing, that is, quickly polling students in a classroom to assess how quickly to proceed with the topic, can also readily be accomplished through online student devices. The move to online testing accompanies the growing use of digital content in education as an important means to improve educational outcomes. A number of national student testing organizations have developed online tests related to state curriculum standards. Below are the critical technology issues that school districts must address as they implement class and school-wide online assessment. Solving these IT barriers will lead to smooth online testing on the way to achieving successful learning for all students.