Research suggests that intervening in the lives of children with an incarcerated parent to preserve and strengthen positive family connections can yield constructive societal benefits in the form of reduced recidivism, less intergenerational criminal justice system involvement and the promotion of healthy child development (Christian, 2009). Since 2008, Central Connecticut State University's (CCSU) Institute for Municipal & Regional Policy (IMRP) has been working with two programs that provide interventions for youth with an incarcerated parent: the Nutmeg Big Brothers Big Sisters (BBBS) program in Hartford and Bridgeport, and the Families in Crisis (FIC) program in Hartford. The Big Brothers Big Sister program is managing the delivery of mentoring services for children with an incarcerated parent. Families in Crisis provides support services to youth with an incarcerated parent and their family. This article summarizes observations offered by some of the children, parent/caregivers, program mentors and agency staff involved with these programs. Their observations can be grouped into six main issues and the primary facilitating factors and constraints that affect these issues. This information should be of interest to other groups across the country offering such programs.