Knowledge of the ecology of the Eastern Black Rail (Laterallus jamaicensis jamaicensis) has remained nearly as elusive as the rail itself. Camera trapping methods facilitated the first study of breeding phenology and chick development, courtship and brood rearing behaviors, and flightless molt phenology and duration. Broods (n = 33) were observed between August 2015 - September 2019. Chicks were capable of flight at approximately 40 days after hatching. Nesting was initiated as early as 17 April 2019 (x̄ = 5 June ± 30.0 SD) and fledging occurred as late as 30 September 2019 (x̄ = 10 August). Behavioral observations combined with phenology data provided evidence of pairs raising two or more broods during a breeding season. Flightless molt (n = 10 adults in molt), which was initiated as early as 15 August 2019 and completed as late as 11 October 2019, was completed within approximately 21 days of initiation. Conservation and management strategies should take into consideration periods of vulnerability, which coincide with increasingly severe and frequent coastal flooding events and hurricanes. It is necessary to understand factors key to fecundity and survival to effectively develop conservation strategies to ensure the persistence of the subspecies.