Transportation-related problems have been consistently reported as barriers to accessing and remaining in HIV medical care, particularly among African American women living in under-resourced areas. With emphasis on the Southern region of the United States, this commentary presents a brief overview of the HIV/AIDS epidemic among African Americans, barriers to remaining in HIV care, and pilot data from a study conducted among African American women living in Mississippi. A small focus group study was conducted to examine the relative influence of transportation-related barriers on attendance and motivation to attend HIV medical care appointments. Eight African American women (mean age of 43.50, SD = 10.82) who were engaged in medical care participated in one focus group session. Time since diagnosis ranged from 6 to 17 years. Participants reported transportation-related barriers that were generally consistent with previous research, including lack of personal transportation, limited financial resources to pay family and friends for transportation or gasoline, and inconveniences associated with sharing van services with other patients. Participants appeared to have learned how to successfully navigate these barriers in order to remain in care. Interestingly, participants reported significant fear of disclosure related to use of transportation services provided by insurance providers and community organizations. Specifically, many of the women indicated that family, friends, and neighbors questioned them about where they were going and why they used taxis. These types of encounters might influence whether individuals utilize available transportation services. Participants provided several recommendations for improving the transportation system. Additional research is warranted to obtain a more representative sampling of opinions among African American women living in under-resourced areas.