Health behavior interventions based on Theory of Planned Behavior address participants' personally-held beliefs, perceived social norms, and control over the behavior. New data are always needed to “member check” participants' decision processes and inform interventions. This qualitative study investigates decision processes around condom use among 81 homeless LGBT youth ages 18–26. Findings indicated considerable endorsement of the conventional policy of always using condoms, promulgated in HIV prevention education targeting this population. Although some participants reported risk behavior in contexts of sex work, survival sex, casual encounters, open relationships, and substance use, most were aware of these risks and consistently safe in those situations. Condoms use boundaries became vulnerable in states of emotional need and negative mood. The only effect participants acknowledged of homelessness on condom use was indirect, through negative mood states. The most prevalent context of condom non-use was with long-term primary partners, a potential area of vulnerability because, of 13 participants for HIV or HCV, nine mentioned how they had been infected, and all nine believed they had acquired it from a primary partner. Findings imply programs should emphasize HIV risk potential within long-term romantic partnerships and mental health services to remediate negative mood states.