Computer-assisted personal interview (CAPI) instruments allow field representatives (FRs) to write their observations during personal interviews. These typically include comments about words or concepts respondents do not understand, as well as additional information about the answers provided. One of CAPI’s advantages is that FRs’ rapport with participants can provide insightful information. In this analysis, I examined field notes for health insurance content from the Survey of Income and Program Participation (SIPP) administered in 2021 and 2022. There were approximately 2,500 household-level case notes grouped into six main topics: private health coverage, Medicare, Medicaid, military-related, other types of coverage, and in cases where coverage ended, the reasons for the loss. Using qualitative analysis, I explored the notes that appeared under each of these topics, identified the most common themes in each one through inductive coding, and grouped them into categories to determine possible issues with the health insurance questions. Results indicated that private coverage had the most case notes, the “Type of Plan” question had the most notes across all questions, and “Not Sure/Don’t Know” was the most common code.