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Preschool education has numerous benefits on children’s development. However, over 17,000 children are expelled annually in the United States (U.S. Department of Education, 2016). Considering the limited research that explores families’ perspectives, our study examined the emotional, financial, and work-family experiences of 23 families whose child was excluded from early childhood programs directly during the enactment of Illinois’ Public Act 100-0105. Our findings revealed that preschool exclusion had negative emotional and financial consequences for families, impacting their daily life, routines, and family dynamics. Additionally, this research sheds light on the supportive role flexible work environments play for families during this unruly time.