A method and system for generating a help file based on failed user queries. A help file generation system collects failed user queries from user computer systems. The generation system assists a developer in identifying failed user queries that are related to a topic. The generation system then updates the entry in the help file for that topic based on the identified user queries. When a help system subsequently uses that help file, it checks the updated entry when searching for a match and will likely find a match to a relevant topic for a user query that previously failed.