Youth are a rapidly growing percentage of the Sub-Saharan African population, and many are economically vulnerable. Financial inclusion for youth, particularly the promotion of savings behavior, is associated with a number of positive social and economic outcomes and is an international priority. However, the majority of youth in Sub-Saharan Africa are not saving, and limited qualitative research exists to aid understanding of the possible explanations. This paper aims to increase the understanding of factors that facilitate and obstruct youth saving by exploring the savings behavior of youth participating in the YouthSave Project in Ghana and Kenya. We conducted in-depth interviews with four triads comprised of youth, a parent or caregiver, and a school stakeholder in each country to develop case studies for the YouthSave Project. Findings indicate that support from parents, school staff, and financial institutions is conducive to youth participation in saving, even though youth participants struggle with limited financial resources and conflicting demands for money. Understanding the reasons, both institutional and individual, that youth in Ghana, Kenya, and other Sub-Saharan countries are not saving is an important part of promoting financial inclusion and greater use of banking services. This study provides first-hand accounts that may be useful for financial institutions, policymakers, and others working to develop youth-friendly financial products and establish financial inclusion policies.