Older adults (age 50 +) are less likely to be tested for HIV and are diagnosed at a later disease stage than younger individuals. To examine the barriers and facilitating factors to testing in this age group, interview data from 35 older men and women who tested HIV positive at age 50 or older were analysed. Participants described a variety of pathways to testing, related to gender, sexual orientation, drug use, and era of the epidemic. Older gay and bisexual men described three trajectories: proactively seeking out testing, delaying testing due to fear and hopelessness, and denying exposure to HIV. Heterosexual drug users and their partners followed two trajectories, depending on the phase of the epidemic: (1) delay due to the lack of knowledge or perceived risk for infection, and (2) delay due to psychological barriers and drug use, despite recognizing their risk. Finally, heterosexual non-drug-users were unaware of their risk. Across risk groups, physical symptoms and encouragement from health care providers were the primary triggers that facilitated testing. The finding that risk perception was a necessary, but not sufficient, condition for undergoing HIV testing suggests that interventions need to reduce barriers and encourage earlier HIV testing among older adults, in addition to promoting risk awareness.