Scholars have theorized that the initial period after military discharge may be a particularly vulnerable time for veterans. Yet, several recent studies raise the prospect that risk for poor adjustment may actually increase rather than decrease over time. The current study examined whether the U.S. military veteran population experiences improvements or declines in their health and broader well-being during the first three years after leaving military service and documented differences based on gender, military rank, and warzone deployment history. A population-based sample of 3733 newly separated veterans completed a survey within three months of separation (Fall 2016), followed by five additional surveys at six-month intervals. Weighted multilevel logistic regressions were conducted to examine changes in the proportion of veterans reporting good health and broader well-being over time. Most aspects of veterans' health and broader well-being worsened over time, with a noteworthy increase in reporting of mental health conditions and a decline in veterans’ community involvement. Declines in the proportion of veterans reporting good health and well-being were most notable for women, with smaller differences observed for other subgroups. The finding that veterans experienced worsening health and broader well-being over time highlights the need for enhanced prevention and early intervention efforts to mitigate these declines. Findings also point to the importance of attending to the unique readjustment concerns of female veterans and other at-risk subgroups. •The proportion of veterans reporting poor outcomes increased over time.•Female veterans were at greater risk for declines in health and broader well-being.•Results highlight the value of bolstering support for new military veterans.•Prevention and intervention efforts should target at-risk veteran subgroups.