In South Africa, nearly one-quarter of cisgender women aged 15–49 are living with HIV, and among them, a significant proportion are pregnant. Maintaining adherence to antiretroviral therapy (ART) during pregnancy and postpartum is crucial for preventing HIV transmission from mother to child. However, women often face multiple challenges that hinder consistent medication use, including pregnancy-related physical changes, mental health struggles, limited social support, and systemic barriers. Digital pill systems (DPS)—medications embedded with ingestible sensors that track adherence—have been implemented in the United States to monitor pre-exposure prophylaxis (PrEP) use among men who have sex with men. While such technology could potentially enhance ART adherence and reduce the risk of mother-to-child transmission in South Africa, its acceptability among pregnant and postpartum women has yet to be explored. Thirty women living with HIV, including 15 who were pregnant and 15 who were postpartum, and who had reported difficulties with ART adherence, were exposed to digital pill systems (DPS) and subsequently participated in qualitative interviews. The interview data were examined using a rapid qualitative analysis method. In the past 30 days, participants reported missing an average of 3.0 (SD = 2.1) doses of ART. Most women found the concept of the digital pill system (DPS) and its elements acceptable, including ingesting a radiofrequency-enabled pill and wearing the accompanying digital Reader, which transmits adherence data to a smartphone app via a lanyard. They felt that DPS could support better adherence and foster accountability, potentially reducing the risk of HIV transmission to their infants. Those who had shared their HIV status with close friends or family generally considered wearing the Reader for a few minutes daily acceptable and appreciated that providers could access their adherence information. The linked smartphone app was also viewed as a helpful reminder for ART collection and ingestion. However, both pregnant and postpartum participants highlighted that the main concern limiting their use—or recommending DPS to others—was the possibility of unintended disclosure of their HIV status due to the visible Reader. Future studies should investigate optimal digital pill Reader designs that enhance usability for this population in South Africa, particularly for individuals reporting suboptimal ART adherence or presenting to antenatal care with unsuppressed HIV RNA.