Background: Protection against postpartum depression is a commonly cited maternal benefit of breastfeeding. However, recent studies have found that negative breastfeeding experiences may actually increase the risk of depressive symptoms. Objective: To investigate women's self-reported associations between breastfeeding experiences and depressive symptoms on a social media platform. Study Design: An electronic search was conducted on Reddit of all original user posts using keywords "breastfeeding" and "depression" from February 2013 to July 2021. Relevant posts and corresponding comments were manually extracted, evaluated for inclusion and exclusion criteria, and analyzed for thematic content. Results: In total, 584 entries was analyzed. Mothers most frequently described difficulty breastfeeding as the cause of new onset mental health symptoms (53%); however, mothers breastfeeding without difficulty were also susceptible (20%). Mothers also reported exacerbated preexisting mental health symptoms-predominantly related to difficulty breastfeeding (17%), but again, others experienced no difficulty (6%). Common words included among all entries were "guilt" (17%), "fail" (14%), "pressure" (7%), "shame" (6%), and "alone" (6%). Among mothers mentioning bonding (n = 99), 58% reported that breastfeeding inhibited infant bonding, versus 1% enhanced bonding; furthermore, 63% reported increased bonding after switching to formula versus 8% unchanged and 6% decreased bonding. Nearly one-quarter (23%) of all posts described inadequate breastfeeding counseling. Finally, 9% of all posts reported a negative experience with health care providers versus 6% a positive experience. Conclusions: Mothers struggling to breastfeed may not experience the classically described benefits of breastfeeding, instead experiencing increased depressive and other mental health symptoms and impaired maternal-infant bonding. Furthermore, limited provider disclosure about potential breastfeeding challenges and alternatives to breastfeeding may exacerbate mental health symptoms associated with breastfeeding difficulties. Balanced information should be presented to mothers contemplating breastfeeding in order to minimize maternal perceptions of "failure."