Deployment can be a significant source of stress for military families. Understanding how families prepare in the face of such stress, and which families are more versus less likely to prepare, is a priority of the Department of Defense. However, there has been scant research on how families prepare for deployments and the factors associated with engagement in preparation activities. The current study is a cross-sectional examination of the proportion of households engaging in deployment preparation activities and family-level and individual-level factors that are associated with these activities in a large and representative sample of married, deployable service members and their families from all military services and components (n = 1,621). Overall, results showed that families reported high rates of engaging in preparation activities, with particularly strong engagement in financial and legal preparation tasks. Talking about deployment to prepare a spouse or child was also relatively highly endorsed but not as frequently cited compared to other logistical preparation activities. Older spouses, officers, active component families, and those with higher marital satisfaction reported greater participation in preparation activities. Families with greater socioemotional difficulties, as indexed by child emotional problems or greater depressive symptoms in the service member or spouse, as well as those with lower spouse-reported marital satisfaction, were more likely to seek professional help. Evaluating the effectiveness of programs in reaching the families that may be least likely to prepare, as well as examining the longitudinal association between deployment preparation and postdeployment family adjustment, is an important area for further inquiry.