Some embodiments track internal actions of a development tool, and actions of a user of the tool. When the user faces a problem, information about the problem state is matched to a mitigation graph that was built from other user's sessions with the tool. Then documentation contextualized to the problem is synthesized, e.g., using machine learning models, and presented to the user. In addition to text and images, the documentation may include interaction points such as hyperlinks or buttons associated with code that mitigates the problem. For example, a mitigation sequence may proactively instruct the tool to perform certain actions such as an install or build or undo, or may automatically operate the tool user interface proactively in place of the user. Mitigation sequences may be sorted, and subjected to cost or outcome desirability prioritization. An administration tool provides mitigation graph management functionality. Personally identifiable information presence is constrained.