Undiagnosed HIV and late HIV diagnosis increase the risk of poor disease prognosis in infected individuals and of onward HIV transmission. It is vital to encourage regular HIV testing among men who have sex with men (MSM), a group disproportionately affected by HIV. A sample of 18 MSM from London and the East Midlands in England were interviewed regarding their perceptions of testing in the following three contexts: genitourinary medicine (GUM) clinics, community settings, and at home using a self-testing kit. The data were analyzed using qualitative content analysis. Perceived stigma from health care professionals, fear of being seen by significant others, and delays in being attended to were seen as barriers to testing in GUM clinics. While community settings were viewed as more accepting of sexual identity, concerns around homophobia and HIV stigma impeded access to testing for some individuals. HIV self-testing alleviated confidentiality concerns, but interviewees doubted the accuracy of the test results and worried about the lack of social support in the event of a reactive test result. Recommendations are offered for improving the acceptability of HIV testing in these contexts.