This study examined the views of parents living with HIV/AIDS (PLWHA) and healthcare providers in Togo, on the appropriateness of HIV-infected fathers disclosing their serostatus to their sons. In early 2016, 177 PLWHA (95 mothers and 82 fathers) and 123 healthcare providers (20 physicians, 24 nurses, 41 nurse’s aides, 13 health counsellors, and 25 psychologists) judged the appropriateness of disclosure in 48 scenarios. These scenarios were composed by systematically varying the levels of four factors derived from previous studies on disclosure of bad news: the visibility of symptoms, the son’s level of psychological robustness, the son’s age, and whether the mother was involved in the decision. Seven qualitatively different positions were found: Depends on Son’s Maturity (20%), Depends on Mother’s Involvement in the Decision and Son’s Maturity (19%), Always Quite Appropriate (16%), Depends on Visibility of Symptoms and Son’s Maturity (15%), Depends on Mother’s Involvement in the Decision (14%), Depends on Son’s Age (9%), and Don’t Tell to Adult Son (7%). Healthcare providers (59% of nurses and 25% of physicians) were more likely than PLWHA (10%) to endorse the view that disclosure is Always Quite Appropriate. These findings suggest that interventions to encourage and support parental HIV disclosure in Togo, and possibly in other sub-Saharan African countries, must not be “one size fits all”, but must be tailored in design and implementation to address parents’ differing views, fears, and needs.