Generating annotated screenshots based on automated tests

Techniques are described herein for generating annotated documentation of a web application based on scripts that simulate tasks performed within the web application. While running each script, an automated testing utility captures individual screens within the web application based on a first set of criteria. The first set of criteria includes capturing a screen after a page loads, before clicking on a DOM element, and before validating the occurrence of an element or event within the web application. An annotation engine then annotates each screen based on a second set of criteria. The second set of criteria includes highlighting each given screen based on the type event and location of the element that triggered the screen capture. The annotation utility additionally visualizes contextual metadata that provides the viewer with a reference of what they are looking at.