Background <p>In 2021, the Education and Training Committee of the Japanese Society for Pharmaceutical Palliative Care and Sciences established an educational training program for pharmacists in palliative care, named Palliative care-Situational Motivating Interactive Learning and Education (pSMILE), based on web-based and face-to-face workshops. The program aims to enhance pharmacists’ knowledge of palliative care and develop communication and cooperation skills.</p> Methods <p>We constructed a web-based pSMILE training program, which was later adapted for face-to-face workshops. This program consisted of two sessions, with the first half at a hospital and the second half at a clinic or community pharmacy. The participants could choose from three learning scenarios. A post-survey (within 1&#xa0;week of the workshop) assessed usefulness, difficulty, length, and satisfaction. Participants also completed a web-based survey on behavioral changes related to daily palliative care following the workshop. Nine items on behavioral changes were assessed before and 1&#xa0;month after the workshop, which was held from April 2021 to March 2024.</p> Results <p>Twelve pSMILE workshops were held during this period (10 web-based and two face-to-face). A total of 296 pharmacists participated, 152 (51.4%) of whom were Board Certified Pharmacist in Palliative Pharmacy, and 292 (98.6%) responded to the before/after workshop survey. Usefulness ratings were 4.39 for Session I and 4.20 for Session II. Satisfaction ratings were high (≥ 4.5), with no significant differences based on affiliation, training format, or certification. All confidence scores of nine daily palliative care behaviors (symptom assessment; multidisciplinary information sharing; proposing pharmacotherapy; polypharmacy intervention; palliative pharmacotherapy with awareness of pharmacokinetics; explanation of delirium; response in the discharge conference; information sharing between hospitals, clinics, and community pharmacies; and pharmacotherapy suggestions in view of the post-discharge) improved significantly post-workshop (<i>p</i> &lt; 0.01), across both web-based and face-to-face workshops. Certified participants had higher confidence scores both before and after the workshop, and each group showed a significant improvement.</p> Conclusions <p>These results suggest that either web-based or face-to-face pSMILE workshops improve the quality of pharmacists’ contribution in daily palliative care. This is the first report on the effectiveness of an academically approved web-based educational program for palliative care pharmacists, comparable to face-to-face workshops.</p>