BACKGROUND: Adverse drug reactions (ADRs) are unintended and harmful events associated with medication use. Despite their significance in postmarketing surveillance, quality improvement, and drug safety research, ADRs are vastly underreported. Enhanced digital-based communication of ADR information to regulators and among care providers could significantly improve patient safety. OBJECTIVE: This paper presents a usability evaluation of the commercially available GuildCare Adverse Event Recording system, a web-based ADR reporting system widely used by community pharmacists (CPs) in Australia. METHODS: We developed a structured interview protocol encompassing remote observation, think-aloud moderating techniques, and retrospective questioning to gauge the overall user experience, complemented by the System Usability Scale (SUS) assessment. Thematic analysis was used to analyze field notes from the interviews. RESULTS: A total of 7 CPs participated in the study, who perceived the system to have above-average usability (SUS score of 68.57). Nonetheless, the structured approach to usability testing unveiled specific functional and user interpretation issues, such as unnecessary information, lack of system clarity, and redundant data fields-critical insights not captured by the SUS results. Design elements like drop-down menus, free-text entry, checkboxes, and prefilled or auto-populated data fields were perceived as useful for enhancing system navigation and facilitating ADR reporting. CONCLUSIONS: The user-centric design of technology solutions, like the one discussed herein, is crucial to meeting CPs' information needs and ensuring effective ADR reporting. Developers should adopt a structured approach to usability testing during the developmental phase to address identified issues comprehensively. Such a methodological approach may promote the adoption of ADR reporting systems by CPs and ultimately enhance patient safety.