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<b>Background/Objectives</b>: While triptans remain the standard of care for moderate-to-severe migraine, the high discontinuation rates and remarkably low prescribing rates of triptans reflect suboptimal therapeutic optimization. <b>Methods</b>: This retrospective cohort study utilized data from Maccabi Healthcare Services (MHS), the second-largest healthcare provider in Israel, spanning 10 years (2012-2022). We identified naïve triptan users aged 21 years or older and evaluated triptan initiation and discontinuation patterns. Median time to discontinuation was assessed using Kaplan-Meier curves. <b>Results</b>: Of 2.8 million MHS members, 91,619 (3.4%) individuals had at least one triptan dispensation or prescription during the study period, including 41,297 triptan-naïve patients who met the study criteria. The median age at triptan initiation was 38.4 years (interquartile range: 28.2-48.0), and 75.6% were female. Overall, the median time to discontinuation was 7.7 months (95% confidence interval: 7.1-8.4). Discontinuation occurred in 70% of the cohort, with approximately 74% of triptan users purchasing only a single triptan formulation throughout the study period. Subgroup analyses by age, sex, socioeconomic status, and anxiety/depression prevalence demonstrated consistent discontinuation patterns across demographic and clinical characteristics, with median time to discontinuation remaining under 12 months in nearly all subgroups. Annual median time to discontinuation consistently remained under 12 months throughout the study period while showing a significant decreasing trend. <b>Conclusions</b>: The low rates of triptan use and high discontinuation rates suggest a possible undertreatment of migraine in Israel. These results highlight the need for improved patient and physician education, and enhanced follow-up protocols.