GuideAutomator is a tool that generates user manuals from Markdown files. It uses Selenium WebDriver to automate taking screenshots of a software's interface as it is being used. This allows the screenshots in the user manual to always match the current state of the software. A pilot study found that while GuideAutomator may take more initial time than traditional tools, it has the potential for better performance over the long term due to its ability to easily keep documentation in sync with software changes through automated screenshotting and Markdown files. Future work includes expanding browser support, adding more API commands, and integrating GuideAutomator with software tests.