Identifying and planning strategies that support a healthy lifestyle or manage a chronic disease often require patient-provider collaboration. For example, people with healthy eating goals often share everyday food, exercise, or sleep data with health coaches or nutritionists to find opportunities for change, and patients with irritable bowel syndrome (IBS) often gather food and symptom data as part of working with providers to diagnose and manage symptoms. However, a lack of effective support often prevents health experts from reviewing large amounts of data in time-constrained visits, prevents focusing on individual goals, and prevents generating correct, individualized, and actionable recommendations. To examine how to design photo-based diaries to help people and health experts exchange knowledge and focus on collaboration goals when reviewing the data together, we designed and developed Foodprint, a photo-based food diary. Foodprint includes three components: (1) A mobile app supporting lightweight data collection, (2) a web app with photo-based visualization and quantitative visualizations supporting collaborative reflection, and (3) a pre-visit note communicating an individual’s expectations and questions to experts. We deployed Foodprint in two studies: (1) with 17 people with healthy eating goals and 7 health experts, and (2) with 16 IBS patients and 8 health experts. Building upon the lens of boundary negotiating artifacts and findings from two field studies, our research contributes design principles to (1) prepare individuals to collect data relevant to their health goals and for collaboration, (2) help health experts focus on an individual’s eating context, experiences, and goals in collaborative review, and (3) support individuals and experts to develop individualized, actionable plans and strategies.