Innovative dispensing products offering real-time medication intake monitoring are being developed to address medication non-adherence. However, implementation of these interventions within the workflow of a community pharmacy is unknown. The purpose of this study was to explore factors affecting implementation of a real-time adherence-monitoring, multidose-dispensing system in community pharmacies. A mixed-method study was conducted with pharmacy staff, who packaged and dispensed medications in smart multidose packages and monitored real-time medication intake via web-portal. Pharmacy staff participated in semi-structured interviews. The Technology Acceptance Model, Theory of Planned Behaviour and Capability, Opportunity, Motivation, Behaviour Model informed the interview guide. Interview transcripts were analyzed thematically and findings were mapped back to the frameworks. The usability was assessed by the System Usability Scale (SUS). Three pharmacists and one pharmacy assistant with a mean of 19 years of practice were interviewed. Three themes and 12 subthemes were generated. Themes included: pharmacy workflow factors, integration factors, and pharmacist-perceived patient factors. The mean SUS was found to be 80.63. Products with real-time adherence monitoring capabilities are valued by pharmacists. A careful assessment of infrastructure—including pharmacy workload, manpower and financial resources—is imperative for successful implementation of such interventions in a community pharmacy setting.