Philosophers and legal scholars are engaged in debates about the implications of artificial intelligence for freedom of expression. This paper analyzes the free speech issues raised by two distinct AI technologies: social media recommendation algorithms and conversational AI (i.e., chatbots powered by large language models). The first part shows that, through their recommendation algorithms, social media platforms control the dynamics of speech visibility in the digital public sphere, making algorithmic recommendation relevant to the philosophy of free speech. The second part turns to conversational AI. It discusses both the reasons for granting or withholding speech rights to artificial agents and users' right to receive information, which may render specific forms of chatbot regulation illegitimate. Throughout, the chapter also considers whether social media platforms or AI developers hold corporate speech rights. Its general aim is to raise rather than settle questions that arise from the rapid development of AI technologies.

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