Background and Objectives Despite the surveilling nature of technologies that allow caregivers to remotely monitor location, movements, or activities, the potential differences in comfort with remote monitoring between caregivers and care recipients have not been examined in depth. On the dyad and aggregate level, we compare preferences of older adult women and their adult children for three remote monitoring technologies. Their assessments of each technology's impact on privacy, safety, independence, freedom, relationship with family member, social life, and identity are also compared. Research Design and Methods This dyadic study used cognitive-based interview probing and value-centered design methods. Twenty-eight individual, in-depth, structured interviews were conducted with 18 women who are Meals on Wheels clients and 10 of their adult children. Results Meals on Wheels participants reported multiple chronic conditions and an average of 1.7 ADL and 3.3 IADL difficulties; two thirds were enrolled in Medicaid. Adult children preferred each technology more than their mothers did and underestimated both their mothers' ability to comprehend the functions of the technologies and the importance of engaging them fully in decision making. Most were confident that they could persuade their mothers to adopt. For both groups, privacy was the most-cited concern, and participants perceived significant overlap between values of privacy, independence, identity, and freedom. Discussion and Implications Studying privacy in isolation overlooks privacy's instrumental role in enabling other values. Shared decision-making tools are needed to promote remote monitoring use consistent with older adults' values and to prevent conflict and caregiver overreach.