Research on children with incarcerated parents has yielded several insights that educators may find useful. In this article, the author highlights three insights from her personal experience: (1) Although having an incarcerated father is the more common experience, having an incarcerated mother is especially likely to disrupt children's everyday lives; (2) Maintaining contact with an incarcerated parent is associated with positive outcomes for children as well as parents, but doing so can be challenging; and (3) Parental incarceration is just one piece of a larger concern: students are growing up in an era of an expanded criminal justice system that shapes not only their day-to-day lives, but also their perceptions of what is possible for their futures. The author closes by advising that in communities where incarceration is common, schools would do well to recognize the extent of the problem, be mindful of challenging dynamics when engaging with students' families, and consider spearheading schoolwide efforts to meet the needs of children with incarcerated loved ones.