With 68% of prisoners recidivating within a three year period, designing and implementing innovative programming within the corrections setting is a necessity. The transient nature of the jail population begets difficulties for its successful implementation and maintenance. Since incarcerated females represent a smaller portion of the population, women, who face different challenges than their male counterparts, often receive less opportunity for programming, especially within the jail setting. Parenting, Prison & Pups (PPP), a program which weaves together an evidence-based parenting curriculum, integrated with the use of Animal-Assisted Therapy (AAT), serves as a model for how to implement innovative programming within the jail setting at both the federal and county level for female prisoners. This paper outlines strategies to employ and discusses challenges that arise during program creation, implementation, and evaluation, which all require consideration prior to starting a new jail-based program. Despite a multitude of challenges, well-developed strategies can advance program goals and outcomes.