The COVID-19 pandemic required academic institutions to quickly transition to online learning and make changes to assessment procedures. This study examines how a school of pharmacy creatively approached the challenge of online assessment while maintaining the standards necessary to prepare practice-ready student pharmacists. To conduct traditional exams, instructors deployed two different types of methods using testing software: a video conferencing technology approach which mimicked pre-pandemic, on-campus proctored exams; or open-book, internet access-enabled exams that ensured academic integrity and rigor through various testing strategies. To assess students' clinical skills, faculty used a combination of techniques such as physical examinations, patient interviews, and patient presentations. To understand the student experience with these assessments, students were surveyed using a 12-item questionnaire. Overall, online video proctoring maintained consistency in exam structure and administration, but required extensive instruction for both students and proctors. Students preferred unproctored, open-book, internet access-enabled, standard time exams versus proctored, closed-book, internet-access disabled, extended time exams. Changes to testing procedures, whether with proctored or unproctored methods, appeared to increase student stress.