A system and related techniques monitor and manage the delivery of automatic help resources to users engaged in search activity. According to embodiments of the invention, automatic help logic may detect the initiation of search activity. The auto help logic may capture, record and examine user behavior and search data to characterize the search progress or effectiveness experienced by that user. When the auto help logic determines that the user has reached an impasse or experienced ineffective results or progress, the logic may generate and present automatic help. If further user behavior does not predict satisfactory progress, further, graduated or tiered help may be generated and presented. According to embodiments of the invention in a further regard, the user may selectively configure the type or content of automatic help which they wish to receive, or turn that facility on or off on a per-session or longer basis.