Chest binding involves the compression of chest tissue for masculine gender expression among people assigned a female sex at birth, particularly transgender and gender non-conforming individuals. There are no peer-reviewed studies that directly assess the health impacts of chest binding, yet transgender community resources commonly discuss symptoms such as pain and scarring. A cross-sectional 32-item survey was administered online to an anonymous, non-random sample of adults who were assigned a female sex at birth and had had experience of binding (n = 1800). Multivariate regression models were used to identify practices associated with self-reported health outcomes. Of participants, 51.5% reported daily binding. Over 97% reported at least one of 28 negative outcomes attributed to binding. Frequency (days/week) was consistently associated with negative outcomes (22/28 outcomes). Compression methods associated with symptoms were commercial binders (20/28), elastic bandages (14/28) and duct tape or plastic wrap (13/28). Larger chest size was primarily associated with dermatological problems. Binding is a frequent activity for many transmasculine individuals, despite associated symptoms. Study findings offer evidence of how binding practices may enhance or reduce risk. Clinicians caring for transmasculine patients should assess binding practices and help patients manage risk.