This study aimed to determine the reasons community pharmacists hesitate to propose drug reduction plans and measures to improve this situation, by using qualitative analysis methods. We surveyed community pharmacists of the Kanagawa Pharmaceutical Association using open-ended questionnaires. On examining the responses of 23 participants, we extracted the following seven categories of reasons for their hesitancy to propose drug reduction and generated the relationships among them; “weak relationship between patients and pharmacists,” “patients have a negative attitude about drug reduction,” “pharmacy workload is complicated and busy,” “pharmacists lack knowledge and experience concerning drug reduction,” “lack of collaboration and information exchange with medical institutions,” “lack of collaboration with doctors,” and “doctors lack awareness of drug reduction.” In addition, 65 specific improvement measures were identified in the questionnaire data. Community pharmacists must be well prepared daily and respond instantly when patients need drug reduction.