Surveillance of communication between incarcerated and non-incarcerated people has steadily increased, enabled partly by technological advancements. Third-party vendors control communication tools for most U.S. prisons and jails and ofer surveillance capabilities beyond what individual facilities could realistically implement. Frequent communication with family improves mental health and post-carceral outcomes for incarcerated people, but does discomfort about surveillance afect how their relatives communicate with them? To explore this and the understanding, attitudes, and reactions to surveillance, we conducted 16 semi-structured interviews with participants who have incarcerated relatives. Among other fndings, we learn that participants communicate despite privacy concerns that they felt helpless to address. We also observe inaccuracies in participants' beliefs about surveillance practices. We discuss implications of inaccurate understandings of surveillance, misaligned incentives between end-users and vendors, how our fndings enhance ongoing conversations about carceral justice, and recommendations for more privacy-sensitive communication tools.