1. A computer-implemented method, comprising: monitoring, via one or more processors, a script being executed to test the functionality of an application, wherein the script includes one or more tags associated with corresponding tags in documentation associated with the application, wherein each corresponding tag indicates a location in the documentation to insert a screenshot of the application; during execution of the script, evaluating text or graphics of one or more content items displayed by the application; upon determining, based on the evaluated text or graphics, that one or more of the content items displayed by the application is associated with a first feature associated with a first tag in the documentation, adding a tag corresponding to the first tag to the script; during execution of the script, when each of the one or more tags is encountered, capturing content items from the application, wherein the captured content items comprise at least a screenshot of the application captured at a point when each respective tag is encountered during the execution of the script; and inserting the captured content items into the documentation at the locations indicated by each of the corresponding tags of the documentation.