We present a novel annotation task evaluating a patient’s engagement with their health care regimen. The concept of engagement supplements the traditional concept of adherence with a focus on the patient’s affect, lifestyle choices, and health goal status. We describe an engagement annotation task across two patient note domains: traditional clinical notes and a novel domain, care manager notes, where we find engagement to be more common. The annotation task resulted in a κ of .53, suggesting strong annotator intuitions regarding engagement-bearing language. In addition, we report the results of a series of preliminary engagement classification experiments using domain adaptation.