We assessed the interference between vaginal ring use and menses among women who participated in the qualitative component of the MTN-020/ASPIRE vaginal ring trial in Malawi, South Africa, Uganda and Zimbabwe (N = 214). A common reason for imperfect ring adherence and premature removal of the vaginal ring cited by participants related to vaginal bleeding or menses. Whereas self-reporting via survey questions suggested that the majority (60%) of women did not mind wearing the ring while menstruating, and did not remove it (91%) during menses, in the qualitative interviews women frequently described removing the ring during menses. Their reasons included hygiene, beliefs that the ring blocked the flow of menstrual blood, fears that the ring would come out with blood or during tampon removal, and concerns around an ‘overburdened’ vagina. Examining women’s narratives and subjective experiences related to menstruation helps build a better understanding of factors affecting ring use and adherence.