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Objectives. To examine associations of workplace leave length with breastfeeding initiation and continuation at 1, 2, and 3 months. Methods. We analyzed 2016 to 2018 data for 10 sites in the United States from the Pregnancy Risk Assessment Monitoring System, a site-specific, population-based surveillance system that samples women with a recent live birth 2 to 6 months after birth. Using multivariable logistic regression, we examined associations of leave length (< 3 vs ≥ 3 months) with breastfeeding outcomes. Results. Among 12 301 postpartum women who planned to or had returned to the job they had during pregnancy, 42.1% reported taking unpaid leave, 37.5% reported paid leave, 18.2% reported both unpaid and paid leave, and 2.2% reported no leave. Approximately two thirds (66.2%) of women reported taking less than 3 months of leave. Although 91.2% of women initiated breastfeeding, 81.2%, 72.1%, and 65.3% of women continued breastfeeding at 1, 2, and 3 months, respectively. Shorter leave length (< 3 months), whether paid or unpaid, was associated with lower prevalence of breastfeeding at 2 and 3 months compared with 3 or more months of leave. Conclusions. Women with less than 3 months of leave reported shorter breastfeeding duration than did women with 3 or more months of leave. (Am J Public Health. 2021;111(11):2036–2045. https://doi.org/10.2105/AJPH.2021.306484) [ABSTRACT FROM AUTHOR]