Software program “help” functionality includes features enhancing its relevance to users. An engine may receive/record context data arising from interactions between a user and the software program. The engine may process that context data to reference a plurality of sources (e.g., official help documentation, user blogs, partner web sites, etc.) and harvest relevant help information. Based upon stored context data and help information available from the plurality of sources, certain embodiments may generate suggested questions allowing further exploration of help issues. Some embodiments may offer help information in the form of an interactive “hotspot” focusing upon a specific UI element (e.g., icon). Processing the context data may allow the engine to assign a particular skill level (e.g., novice/intermediate/expert) to individual users, tailoring the help information to that skill level. The interactive nature of the help functionality may enhance its use in conjunction with complex workflows encountered in many software programs.