This study examined how family factors that diminish feelings of loss (frequent communication) and reflect system-level adaptation (effective household management) during deployment were associated with enhanced resilience and fewer vulnerabilities during reintegration and, ultimately, the promotion of family functioning following deployment. Multiple reporters from active duty (AD) military families (N = 214 families; 642 individuals) were examined, including AD members, civilian spouses, and their adolescent offspring. Most service members were men and enlisted personnel (95.3% male; 87.9% enlisted). Most AD and civilian spouses were between the ages of 31 and 40 (68.2% and 72.4%, respectively). Adolescent gender was relatively equal between boys (46.3%) and girls (53.7%), and their average age was 13.58. A SEM assessed the influence of communication frequency (reported by both AD and civilian spouses) and household management during deployment (reported by civilian spouses) on subsequent family functioning (reported by AD spouse, civilian spouse, and adolescent). The mediating role of positive and negative aspects of post-deployment family reintegration (reported by AD spouse, civilian spouse, and adolescent) was also assessed, as indicators of family resilience and vulnerability. Communication during deployment and civilian spouses’ household management during deployment were associated with multiple family members’ reintegration experiences. In turn, reintegration experiences were linked to self-perceptions of subsequent family functioning and, in some cases, other family members’ perceptions of family functioning. Similarities and differences among family members are discussed. While deployment and reintegration create systemic family changes and challenges, results indicated opportunity for growth that can reinforce connections between family members.