Young mothers constitute a vulnerable population in Canada. Teens with children are at significant risk of subsequent pregnancy, a dynamic that can exacerbate health, emotional, and socio-economic challenges. We aimed to understand better the dynamics shaping “rapid repeat pregnancy” among young mothers in Ottawa, explore young mothers’ subsequent pregnancy experiences, and identify how services could be improved in Canada’s capital. In 2016, we conducted in-depth interviews with 10 young mothers and semi-structured interviews with 10 key informants working with pregnant and parenting youth. We analyzed interviews for content and themes using a multi-phased, iterative process. Four major themes emerged: (1) young mothers often plan their pregnancies actively or passively; (2) violence before, during, and after pregnancy is common; (3) mental health and substance abuse issues shape pregnancy risk; and (4) becoming pregnant often serves as a source of motivation for young mothers. Our results further indicate that young mothers have difficulty finding youth-friendly, non-judgmental support services and that integrated, multidisciplinary services offering individually tailored support and building on women’s strengths will likely be more successful in helping young mothers prevent subsequent pregnancies. Increasing awareness about existing services and supporting efforts that approach teen pregnancy comprehensively and holistically appear warranted.