Background/Objectives: American Tegumentary leishmaniasis typically presents as a single ulcerative lesion, but atypical clinical forms exist with diverse physiopathology and treatment responses. Disseminated cutaneous leishmaniasis is a less common presentation that is often challenging to treat and for which evidence-based clinical decisions are scant. A better understanding of treatment response may support the development of alternative therapeutic strategies. This study reports a retrospective cohort analysis using a time-to-event outcome to compare disseminated leishmaniasis with localized cutaneous leishmaniasis using a multivariate model. Methods: A total of 366 patients were screened for inclusion between 2014 and 2024, of whom 123 met the inclusion criteria. Results: After adjustment for age and sex, patients with disseminated cutaneous leishmaniasis had a significantly longer time to healing than those with localized cutaneous leishmaniasis (HR = 0.29; p = 0.021). Conclusions: Disseminated cutaneous leishmaniasis seems to be an important predictor of poorer clinical outcomes with prolonged healing time. New therapeutic strategies are urgently needed to address this issue.