Many firms engage in activities aimed at making prices less transparent – tactics that may be referred to collectively as price obfuscation. Existing theory does not explain the substantial heterogeneity that exists both within and across industries with respect to the prevalence of these practices. The essays herein thus seek to shed further light on this phenomenon. In particular, I address several interrelated questions: what incentives drive firms to obfuscate in the first place, what are the potential consequences (if any) of doing so, and how do these tradeoffs vary depending on firm characteristics and market conditions? Novel empirical results are drawn from U.S. hotel industry data in Chapters 1 and 2; in Chapter 3, I synthesize existing price obfuscation literature from a range of disciplines and provide several illustrative case studies. Taken together, these three essays build toward a more comprehensive theoretical framework for understanding why, in practice, some firms utilize obfuscation (and deceptive tactics more broadly) while others do not.