The subject disclosure pertains to systems and methods that facilitate monitoring of data collections and related data retrieval systems as well as generating recommendations for enhancing performance and utility of such systems. In aspects, the systems and methods described herein evaluate data retrieval performance by identifying unsuccessful search queries and mapping such queries to appropriate content in a data collection. To facilitate such evaluation, similar queries can be grouped and treated as equivalent. Similarity of queries can be determined based upon search terms. For example, queries whose search terms only vary syntactically can be combined in a group. Such groups can include search information related to multiple users, increasing reliability of recommendations based upon such groups. In further aspects, recommendations for adding content can be generated in conjunction with any mapping recommendations.