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Background: An estimated 44–69% of female sex workers (FSW) in South Africa are living with HIV, among whom 39% are virally suppressed. Digital technologies—increasingly advanced and accessible to marginalized populations—present new opportunities to improve the HIV care continuum. The objective of this study was to explore potential facilitators and barriers to incorporating mobile phones and advanced technologies (e.g., biometric identification methods, mobile phone applications for social media and other uses, and chatbots) to deliver HIV-related interventions to cisgender FSW living with HIV in Durban, South Africa. Methods: Four semi-structured, focus group discussions (FGDs) were conducted with 22 cisgender FSWs in December 2018. Participants were recruited from the ongoing Siyaphambili trial using maximum variation sampling to optimize diversity in participant age and sex work venue. FGDs were audio recorded in isiZulu, and translated and transcribed into English. Transcripts were inductively coded using thematic analysis and sub-themes were iteratively refined to connect and evaluate the saliency of codes. Results: Phone ownership was motivated by a desire to remain safe and to connect with family, peers, and clients. When FSW did not have access to a mobile phone, they reported sharing phones with their peers, though sharing only occurred under specific conditions. Still, to integrate mobile phones into HIV care, FSW identified consistent access to mobile phones as a key barrier. Mobile phone turnover due to frequent selling of phones to meet other financial priorities, substance use, and theft were common. To integrate advanced technologies into HIV care, FSW identified convenience, security, and additional opportunities for social support as the main facilitators. For example, FSW described how biometric identification at clinics could eliminate the need to retain a clinic card. FSW also described how chatbots could easily set medication alarms or be available to assist in emergencies. Barriers for advanced technologies included maintaining privacy, potential threats to security, and cost. Conclusions: FSWs were receptive to digital technologies for HIV care and beyond, but they also described many barriers such as inconsistent phone ownership and threats to privacy. As phone ownership grows and HIV programs increasingly leverage digital tools, strong considerations are needed to ensure the most vulnerable are not systematically excluded.