This study aims to give insight into how urban homeless youth choose whether to trust professionals, and to describe the characteristics of a professional they view as deserving of trust. The authors used a convenience sample of 18-21 year olds recruited from an urban shelter serving homeless youth, most whom have had a history of emotional trauma, exploitation, and abuse. Ethnographic interviews were conducted in 2 phases. Of the 49 interviewed, approximately 92% were African-American, 6% Latino, 2% white. Youth revealed 5 key points about trust formation, offering context to when and how much they were willing to self reveal to a professional. 1) Initial interactions are based on level of need. Youth withhold sensitive information if there is no urgent issue, whereas in crisis they “take a risk.” Trust is gained quickly if the professional is helpful and displays the traits that earn trust, whereas it is violated if the professional is unhelpful or disrespectful. 2) When no immediate need is present, youth “observe” the professional’s interaction with others and may share mildly sensitive information while carefully observing the person’s reaction and behaviors. 3) If the professional appears trustworthy after this period, many youth report “testing” him/her by slowly revealing sensitive information to see if confidentiality is broken or they feel judged. 4) A successful outcome after sharing during a crisis may allow the observation and testing periods to be skipped. 5) A violation of trust at any point causes serious damage, often leading to withdrawal and anger. It may sometimes lead to a second closely monitored chance. In every stage, youth observe for the key professional behaviors of honoring privacy, being honest, being authentically respectful, and maintaining a nonjudgmental stance. There were divergent opinions on whether a person with shared life experience was easier to trust; most stated that it was more important that the professional display genuine concern for youths’ success. (Authors) The authors conclude that homeless youth have had challenging, often painful, experiences with adults, they go through a thoughtful process that includes observation and testing before taking the chance of revealing sensitive information. Professionals who display honesty, respect without judgment, and maintain privacy may be deemed trustworthy.