Changes in lifestyle can have positive effects on treating type 2 diabetes (T2D), like sporting or healthy eating. Therefore, a person diagnosed with T2D is often advised to make healthy choices throughout the day, in addition to other interventions such as medication. To do this, he or she needs health information to support decision-making. Literature describes ample categorizations of types of (health) information behavior and theoretical models that explain the factors that drive people to search for, encounter or avoid information. However, there are few longitudinal studies about triggers and factors in daily life that affect health information behavior (HIB). This study was set up to identify triggers, actions and outcomes for active, passive and avoidant HIB situations in daily life among Scots with Type 2 diabetes (T2D) to identify points of attention for communication strategies. Twelve participants took part in a four-week diary study. Every day, participants received an online diary form to describe active, passive or avoidant HIB situations. Data collection resulted in 53 active, 120 passive and 25 avoidant diary entries. Seven active HIB contexts (e.g., experiencing symptoms, cooking dinner, sports training) and five passive HIB contexts (e.g., home, work, medical facility) were identified. Four motivations for avoidance were found (e.g., time constraints, no health trigger). These results can be used to supplement the theoretical models of health information behavior. Furthermore, health professionals can use these results to support their clients with T2D in the self-management of their health, by guiding them to trustworthy sources of health information and lowering barriers for searching health information.