Contextualizing care is a process of incorporating information about the life circumstances and behavior of individual patients, termed contextual factors, into their plan of care. In 4 steps, clinicians recognize clues (termed contextual red flags), clinicians ask about them (probe for context), patients disclose contextual factors, and clinicians adapt care accordingly. The process is associated with a desired outcome resolution of the presenting contextual red flag. To determine whether contextualized clinical decision support (CDS) tools in the electronic health record (EHR) improve clinician contextual probing, attention to contextual factors in care planning, and the presentation of contextual red flags. This randomized clinical trial was performed at the primary care clinics of 2 academic medical centers with different EHR systems. Participants were adults 18 years or older consenting to audio record their visits and their physicians between September 6, 2018, and March 4, 2021. Patients were randomized to an intervention or a control group. Analyses were performed on an intention-to-treat basis. Patients completed a previsit questionnaire that elicited contextual red flags and factors and appeared in the clinician's note template in a contextual care box. The EHR also culled red flags from the medical record, included them in the contextual care box, used passive and interruptive alerts, and proposed relevant orders. Proportion of contextual red flags noted at the index visit that resolved 6 months later (primary outcome), proportion of red flags probed (secondary outcome), and proportion of contextual factors addressed in the care plan by clinicians (secondary outcome), adjusted for study site and for multiple red flags and factors within a visit. Four hundred fifty-two patients (291 women [65.1%]; mean [SD] age, 55.6 [15.1] years) completed encounters with 39 clinicians (23 women [59.0%]). Contextual red flags were not more likely to resolve in the intervention vs control group (adjusted odds ratio [aOR], 0.96 [95% CI, 0.57-1.63]). However, the intervention increased both contextual probing (aOR, 2.12 [95% CI, 1.14-3.93]) and contextualization of the care plan (aOR, 2.67 [95% CI, 1.32-5.41]), controlling for whether a factor was identified by probing or otherwise. Across study groups, contextualized care plans were more likely than noncontextualized plans to result in improvement in the presenting red flag (aOR, 2.13 [95% CI, 1.38-3.28]). This randomized clinical trial found that contextualized CDS did not improve patients' outcomes but did increase contextualization of their care, suggesting that use of this technology could ultimately help improve outcomes. ClinicalTrials.gov Identifier: NCT03244033.