One of the new business phenomena that has emerged as the Internet era has fully matured is the rise of so-called infomediaries. The success of infomediaries—commercial entities that enhance the likelihood of transaction matching by collecting, adding value to, and providing information needed by both consumers and suppliers through high-performance media such as the Internet—begins with the accumulation of high-quality information, and consumers provide their personal information to infomediaries when they can obtain appropriate benefits. However, as consumer awareness of the value of personal information and the risks of privacy violation has expanded, collecting high-quality information has become an increasingly difficult challenge for infomediaries. Moreover, in early-stage usage situations like those in Korea, where intrinsic cues about an infomediary's information brokerage capabilities are difficult to assess, information-poor consumers may refuse to provide information without distinguishing between good and poor infomediaries, raising the possibility of market failure that is particularly disadvantageous for superior infomediaries. Consequently, research questions arise regarding the following: What cues do consumers use to identify superior infomediaries under conditions of incomplete information? What should superior infomediaries do, and how, to obtain consumer cooperation (information provision)? In this study, through an exploratory survey, the extrinsic cues that consumers use to infer an infomediary's service capabilities in early-stage usage situations were investigated. Among these cues, a signaling game was constructed centering on free content—a new signaling mechanism not previously addressed in existing signaling research—to analyze the process by which infomediaries signal their capabilities to consumers through free content under conditions of information asymmetry. Analysis of this game's equilibrium reveals that under conditions of incomplete information, superior infomediaries with excellent information brokerage capabilities "over-provide" free content to signal their capabilities to consumers, while under information symmetry, they choose the optimal level considering the costs and benefits of providing free content.