Mediated communication enabled by information technology has immense potential to positively affect personal health. Although existing theories of technology use and adoption have advanced our understanding of information technology, they do not fully address voluntary adoption in community settings, adoption across the lifespan, and privacy concerns. Drawing on evidence collected during more than five years of field research, we start to address those issues, especially as they pertain to HealthIT (e.g. mHealth, e-Health, and/or connected health) use. Our goals include advancing theoretical discussions on technology acceptance and offering practical applications useful for medical professionals serving patients of all ages. We discuss our findings related to mandatory adoption learning heuristics, pressured voluntary adoption, digital immigrants' self-reported technology use and skill, perceived versus actual support, concerns about online privacy and information sharing, potential loss of control over personal information, online-offline boundary incongruence, and adoption barriers related to technological features.