In April 2020, a survey was conducted among Slovenian military families, being one of the first surveys to be carried out in the country after the outbreak of the pandemic. The military was labeled a crucial institution in the efforts to combat the SARS-CoV-2 virus and was appointed to various activities, leading to a considerable increase in its workload. The burden of care and unpaid work at that time also intensified, becoming shifted onto the military family, particularly civilian female spouses. The survey’s purpose was to measure how military families evaluated their success in balancing between working from home, household work, childcare, and home schooling during the pandemic lockdown. The risk factors were observed on the micro (i.e., lack of extended family support, institutional childcare, and school lockdown) and macro (i.e., military support, national support measures) social levels. The analysis reveals that when it comes to military families the greatest price has been paid by female civilian spouses. The number of children and their age influence parents’ self-evaluation of their success with work–life balance. The results show that big families and families with primary school children have been struggling the most during the lockdown. Surprisingly, dual-serving families felt the most successful.