Statistics show that Americans consistently turn to Google and other search engines to answer their most personal and private concerns, yet a new investigative tool risks law enforcement having vast discretion in the access of this data. With a keyword warrant, law enforcement can request from a search engine provider (usually Google) a list of probative search queries that users made over a specified time period. Such warrants are beginning to face legal challenges, and so far, courts seem reluctant to recognize the constitutional implications—instead leaving law enforcement with greater potential discretion over their use. This Note assesses the constitutionality of keyword warrants by arguing that the underlying investigative process falls within the ambit of the Fourth Amendment. It further concludes that keyword warrants may pass constitutional muster in a narrow set of circumstances, but that doing so requires robust judicial oversight. Finally, this Note proposes a novel approach that magistrates can adopt to ensure that keyword warrants comply with core constitutional safeguards. This Note contributes to current discourse by becoming the first piece of scholarship to urge the recognition of Fourth Amendment implications of keyword searches while also envisioning a narrow case in which they may be constitutional and proposing a pragmatic solution to ensure the protection of Americans’ privacy interests.