A system and method for incorporating software modules into a website or other information source that is searchable and updateable, which helps to create a dynamic user assistance environment. The system searches based on context/category sensitive natural language requests. This dynamic environment becomes “smarter” over time and will track questions and answers by a number of methods to assure the answers are up to date and that there is a high confidence match for the user's inquiry. The entire collection of data resides in a centralized location where the information can be leveraged to answer a user's question and aid in the creation of question/answer pairs for later use. Additionally, the assistance system supports a method for incorporating new informational content and answers to unanswered questions, for example by authorized support persons, that are categorized and stored in the existing system for later reference and use.