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The purpose of our partnership with the UHN OpenLab was to discover the barriers involved with automating the sporadic release of clinical practice guidelines (CPGs) into the Innovate Guidelines Application (IGA). The problem is considered wicked—interlocking challenges cannot be addressed by a single solution. Accordingly, the goal was to explore the barriers of stakeholders and specialization groups, general guideline issues, and the considerations of healthcare professionals and public perception. An initial literature review was conducted to discover unidentified problems before a first draft of the systems map was created. Subsequently, connections were formed across problems and each was categorized based on degree of complexity. A white paper was drafted to complement the systems map, explain the problem clearly, and highlight areas to be further explored. The recommendation brief outlines where further action could be taken. Key findings of the white paper include that guideline standardization and the use of automation were significant complications with the project. The lack of standardization between guidelines makes categorizing them tedious as there are few common elements or formats. This problem is further perpetuated by new guidelines, which continue to be made without commonality between producers. A recommendation for the UHN OpenLab team is the use of automation software to sort pre-existing guidelines efficiently. Additionally, there should be a push for a checklist screen to generate commonality between future guidelines. This list for guideline producers would act as a completion and quality control marker while still allowing freedom in design and format.