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Scholarly debate around social media and free speech has evolved around two dominant themes: the role of social media platforms in enabling political speech and dissent; and the role of governments in blocking and censoring content on social media platforms. Decidedly less attention has been paid to the role that social media companies play in enabling or restricting free expression and global information flow by their user policies. To fill that gap, this paper studies how Twitter, a social media platform recognized as a mobilizing tool, enacts its user policy when censoring speech, and the economic and political implications of the censorship. Taking a case study approach, this paper analyzes a number of high profile censorship instances on Twitter, to find out to what extent the company follows its user policies and commitments to free expression when enforcing censorship. Findings of this study indicate that Twitter’s user policy is enacted in an inconsistent manner, and that often economic incentives and political pressure take precedence over values of free expression.