Previous research has indicated that approximately 25% of the 30,000 youths emancipated from foster care each year experience negative outcomes including poor education attainment, limited employment opportunities, homelessness, lack of access to healthcare, and poor social networks. Despite the existence of federal legislation that requires foster care agencies to assist foster youths to make the transition to independent living, research has revealed that the current transitional planning process is not effective. There is a gap in the current literature regarding qualitative research on youths' shared experiences of the transitional planning process as they transit out of foster care. This study examined youths' experiences with the transitional planning process and the degree to which the plan mitigated homelessness after emancipation. The study employed a descriptive phenomenological approach. Participants were 10 youths age 18 to 21 who emancipated from the Department of Human Services, Children and Youth in Philadelphia, Pennsylvania, foster care system within the past 3 years. Purposive sampling was used to recruit participants and semistructured interviews were used collect the data. Social capital theory was used to guide the study. Data were inductively analyzed with management assistance from NVivo software. Results indicated that participants experienced challenges during transition in housing, education attainment, employment, physical or mental health, and finding mentors and continuing support. Participants offered suggestions for improving the transition planning process. Findings from this study can be used to enhance social change initiatives by providing insight into what youths need to better prepare them for independent living.