Software documentation is the key to software quality and security. Writing better and more up-to-date documentation for code libraries and software is necessary to ensure these benefits. This task is become more difficult and time consuming as software increase in size and complexity. Yet, the task of writing the documentation in smaller teams often falls on the shoulders of the developer writing the code. Without tools to know what part of the documentation to update, how to validate its quality, or to track the evolution of the documentation over time, the quality of the documentation will eventually decline as it becomes more and more outdated. Over a three-month long Honours Project, I built and validated an automated tracking tool for software documentation as an attempt to solve this problem.