The present research examines the understudied impact of the regulatory environment on the manifestation of Entrepreneurial Orientation (EO) among firms within an emerging market context. Results from an exploratory sample of 432 Russian Small and Medium-Sized Enterprises (SMEs) suggest that key aspects of the regulatory environment may deserve further attention in future research. Controlling for the level of compliance by a given Russian SME, the perceived protection of private property rights was observed to have a marginally significant direct positive effect, whereas the perceived strength of contract law is shown to exhibit a marginal negative relationship with EO among Russian SMEs. In terms of operating within this emerging regulatory context, the perceived availability of governmental contracts had a marginal positive effect on EO. Finally, stressing the importance of 'who you know is more important than what you know', relationships with government officials had a very strong positive effect on EO.