The outbreak of the COVID-19 pandemic has led to restrictions on access to face-to-face classes in schools and postsecondary institutions across the globe. As educators seek online means to pursue learning opportunities, learning management systems (LMSs) are becoming increasingly important. LMSs have traditionally relied on asynchronous methods such as email, bulletin boards, and blogs to communicate with students. These tools have also been used to facilitate student assessment, such as the collection of assignments and the delivery of feedback. However, certain types of summative assessments cannot be accomplished online using asynchronous tools. Observations, interviews, and proctored examinations require a more synchronous approach to be considered valid in an online learning environment. Through a reflective lens, this chapter explores the case for incorporating synchronous tools such as video conferencing and live chat into online testing strategies to improve the validity and effectiveness of assessment delivery in a COVID-19 world.