Provided is a method for generating and updating screenshots within computer software documentation. The disclosed techniques enable software documentation to insert up-to-date screenshots either upon installation of the corresponding software, dynamically when the documentation is used, or in some combination of the two approaches. In one embodiment, the computing system or application detects when screenshots have been modified and regenerates screenshots within affected documentation. Documentation is created that includes text and macros. The macros provide for the inclusion of screenshots within the documentation. Each macro includes information about where an associated screenshot is to be captured, the steps necessary to capture the screenshot and the location within the documentation where the screenshot is displayed. Also included in association with the macros is configuration information necessary to generate the appropriate screenshot.