On any given night in 2015, over 500,000 people were homeless and 31% of them slept in unsheltered locations. Given the seriousness of this situation, the purpose of this research study was to test a student prototyped, portable shelter with six men who were homeless. Qualitative interview questions were developed by the research team. Six, open-ended questions for baseline interviews and 11 open-ended questions were used after the men slept in the shelter for two nights. The men ranged in age from 25 to 56 years and had been homeless for 1–5 years. Two of the men were African American and four were Caucasian. Several themes emerged from the data collected: dignity, safety, security, control, privacy, and portability. While the research team thought that carrying the shelter on your back was a novel idea, none of the men liked this design feature. The majority of men carried backpacks and stated that individuals who are homeless would not carry the shelter, rather they would hide it. Dignity also became an issue, as these men did not want to advertise their homeless condition by carrying the shelter. Safety and security from the “law,” “animals,” and “other homeless” people were other concerns. All of the men liked the privacy and control the shelter provided as it allowed them to eat, sleep, and talk on their cell phone when they wanted to. Giving these men a voice and allowing them to actively sleep in the prototype gave the research team a better understanding of design suggestions needed for portable homeless shelters.