Military family members are subjected to profound and unique stressors, especially during times of war. Advancing research with regard to military families has the potential to provide information that will help programs and practitioners to better promote the wellbeing of military families through identifying needs and coping strategies unique to these families. The purpose of the current study was to examine the nature of stressors and coping strategies among military families. The participants for this study were 23 parents, of dependent children, who were either active military personnel or spouses of active military personnel. Guided by transactional theory of stress and coping, and family systems theory perspectives, a survey was created with open-ended questions that tap into stressors and coping strategies specific to the family and military family transitions. The current study utilized a qualitative approach to analyzing the answers provided by the participants by identifying emergent themes. The themes identified reflected challenges and coping mechanisms that fell into three categories: couple, parental, and family-level stresses and coping strategies. Couple themes included communication challenges, couple coping through communication, and being a team. Parental themes included increased parent workload and stress, and stigma associated with being a military mother or in a dual military relationship with a military mother. Lastly, the family-level themes included stress associated with impending separation, and reintegrating the deployed family member back into the family system after deployment. These themes reflect both challenges unique to military families and coping strategies that help families adjust despite the stressors they face. The prevalence of challenges expressed in this study suggests that military families may benefit from further intervention and prevention programs, or that existing programs could be enhanced to better address the above challenges and teach coping strategies that appear to be helping some families adapt.