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This qualitative study examined the educational experiences of teenage mothers during the COVID-19 pandemic. The onset of the pandemic necessitated that educational leaders move beyond traditional models to establish a new educational infrastructure, demonstrating a capacity for unimaginable innovation. There is a lack of literature examining how teenage mothers balanced their roles as caregivers and students while adjusting to a new educational format. The research question guiding this study was: “How are previous high school experiences viewed by women aged 18-22, who were teenage mothers during the COVID-19 pandemic, dropped out of high school and were currently enrolled in a General Education Development (GED) or High School Diploma Program (HSDP)?” Participants were recruited from two alternative schools. Generic qualitative inquiry was the research methodology applied in this study. This qualitative study utilized interviews to gather data from the participants in this study about their high school experiences, leading up to them dropout of high school. The sample was six women aged 18-22, who were teenage mothers, dropped out of high school enrolled in a GED or HSDP at two alternative high school in a school district located in the Midwest. Data collected in this study identified participants’ educational experiences during the COVID-19 pandemic were not positive. Themes from the experiences that emerged from the data analysis were remote learning format challenges, struggle with belonging, and adapting to new educational realities. The study answered the research question. Findings included teenage mothers who struggled like many teenagers during the COVID-19 pandemic. However, the added contributors to their struggles were related to navigating a new learning platform while balancing responsibilities as caregivers and students. Limitations from this study included the lack of research on the specific topic, the small sample size and the sample emerging from only two schools in one geographical location.