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Background Problem-oriented documentation is an accepted method of note construction which facilitates clinical thought processes. However, problem-oriented documentation is challenging to put into practice using commercially available electronic health record (EHR) systems. Objective Our goal was to create, iterate, and distribute a problem-oriented documentation toolkit within a commercial EHR that maximally supported clinicians’ thinking, was intuitive to use, and produced clear documentation. Materials and Methods We used an iterative design process that stressed visual simplicity, data integration, a predictable interface, data reuse, and clinician efficiency. Creation of the problem-oriented documentation toolkit required the use of EHR-provided tools and custom programming. Results We developed a problem-oriented documentation interface with a 3-column view showing (1) a list of visit diagnoses, (2) the current overview and assessment and plan for a selected diagnosis, and (3) a list of medications, labs, data, and orders relevant to that diagnosis. We also created a series of macros to bring information collected through the interface into clinicians’ notes. This toolkit was put into a live environment in February 2019. Over the first 9 months, the custom problem-oriented documentation toolkit was used in a total of 8385 discrete visits by 28 clinicians in 13 ambulatory departments. After 9 months, the go-live education and EHR optimization teams in our health system began promoting the toolkit to new and existing users of our EHR resulting in a significantly increased uptake by outpatient clinicians. In April 2022 alone, the toolkit was used in more than 92 000 ambulatory visits by 894 users in 271 departments across our health system. Conclusions As a health-system client of a commercial EHR, we developed and deployed a revised problem-oriented documentation toolkit that is used by clinicians more than 92 000 times a month. Key success elements include an emphasis on usability and an effective training effort.