Insurers should expect additional hurdles in the area of social media advertising compliance. To the extent that insurers are pursuing business in social media marketing channels and policyholders are increasingly meeting their insurance needs through social media utilities, it is imperative that insurers anticipate and employ comprehensive solutions for compliance issues that will invariably arise. Do state insurance advertising laws take in social media? What does the current social media regulatory landscape look like? To what extent are insurers and producers using social media? What are some problematic scenarios for insurers and policyholders? This paper tackles these insurance advertising and other social media compliance questions and arrives at the following conclusion: Insurers who do not invest in social media compliance solutions will find themselves at a distinct disadvantage not only in the marketplace but with regulators as well.