Qualitative interviews were conducted with mothers (N = 47) who had disclosed their HIV status to their child. Mothers described their preparation and the process of the disclosure event, and discussed any regrets they had about disclosing or the process of disclosing. They were also asked what advice they had for other HIV-positive mothers who were trying to determine whether to disclose their serostatus to their young children. Overall, the majority of the mothers (68%) did not regret disclosing their HIV status. Regrets fell into five categories: preparation, timing, context, content, and outcomes of the disclosure event. Based on these findings, mothers who have not disclosed their serostatus to their children need assistance with behavioral practice and support in order to prepare for the process. Furthermore, follow-up support for the children may be beneficial.