The Global War on Terror began as a result of the 2001 attacks on the World Trade Center. Due to repeated and often long deployments, soldiers and families have been affected. Mental health and family unit studies indicate that children of military service members can experience emotional and behavioral distress. Few studies have examined deployment through the lens of education. Therefore, this study of kindergarten teachers’ experiences working with children of a deployed parent fills a gap in understanding deployment in an educational setting. This study utilized a basic qualitative design and is framed in attachment theory and ecological systems theory. This study selected 15 kindergarten teachers with at least two years’ experience working with students during a parental deployment. Data were collected through individual semi-structured interviews, interviews were transcribed by hand, and data were analyzed through the use of NVivo 12. The findings indicate that teachers described students as displaying internalizing and externalizing behaviors and that the non-deployed parent’s handling of deployment influenced the student. Other findings indicated that relationship building with students during deployment was important and often counselors, peers, and parent contacts were utilized. Teachers, according to study findings, employed no specific teaching approaches but used holidays and classroom activities to teach and allow students to express themselves during a deployment. Student needs and behaviors were found to be a challenge, as was teachers’ lack of military background and understanding. More extensive professional development was found to be a need for teachers in supporting students with a deployed parent.