Tabitha Haly, born with spinal muscular atrophy, faced significant challenges throughout her life but successfully built a career in finance, eventually becoming a vice president at JPMorgan Chase. Her achievements were jeopardized when her Medicaid benefits, crucial for her home health aides, were abruptly terminated due to complications with Social Security’s work-support programs. Despite adhering to the rules of Section 1619(b) of the Social Security Act, which allows continued Medicaid eligibility while working, a lack of understanding about this provision within the Social Security Administration (SSA) led to confusion and the loss of her benefits. Haly’s struggle to navigate the system included reaching out to elected officials and advocates, ultimately resulting in her resignation from her job to qualify for state Medicaid benefits. With the help of the National Organization of Social Security Claimants’ Representatives, her case highlighted the complexities and inadequacies of the system, particularly for those with disabilities who wish to work. The article emphasizes the critical role of advocacy and the need for better awareness of support programs that enable individuals with disabilities to participate in the workforce while receiving necessary care.