While it has long been recognized that health care professionals play an important role in supporting self-care management in chronic illness, the nature of that support is not well understood. This paper represents an analysis of findings drawn from qualitative research into the development of self-care decision-making expertise in adults with longstanding Type I diabetes, specifically addressing ways in which health professionals' interactions support or fail to support such processes. These findings highlight issues associated with the disease trajectory, the assumptions about intended outcome, and the complex contexts in which individuals live with chronic disease, illustrating the manner in which varying kinds of support may be required at different points within the learning process. They further challenge notions of standardized communication and informational strategies, demonstrating the complexities inherent in the support needs of chronically ill persons as they change over time and context.