Data-to-Care (D2C) uses surveillance data (e.g., laboratory, Medicaid billing) to identify out-of-care HIV-positive persons to re-link them to care. Most US states are implementing D2C, yet few studies have explored stakeholders’ perspectives on D2C, and none have addressed these perspectives in the context of D2C in jail. This article reports findings from qualitative, semi-structured interviews conducted with expert stakeholders regarding their perspectives on the ethical challenges of utilizing D2C to understand and improve continuity of care among individuals incarcerated in jails. Participants included 47 professionals with expertise in ethics and privacy, public health and HIV care, the criminal justice system, and community advocacy. While participants expressed a great deal of support for extending D2C to jails, they also identified many possible risks. Stakeholders discussed many issues specific to D2C in jails, such as heightened stigma in the jail setting, the need for training of jail staff and additional non-medical community-based resources, and the high priority of this vulnerable population. Many experts suggested that the actual likelihood of benefits and harms would depend on contextual details. Implementation of D2C in jails may require novel strategies to minimize risk of disclosing out-of-care patients’ HIV status.