Online users are increasingly exposed to chatbots as one form of AI-enabled media technologies, employed for persuasive purposes, e.g., making product/service recommendations. However, the persuasive potential of chatbots has not yet been fully explored. Using an online experiment (N = 242), we investigate the extent to which communicating with a stand-alone chatbot influences affective and behavioral responses compared to interactive Web sites. Several underlying mechanisms are studied, showing that enjoyment is the key mechanism explaining the positive effect of chatbots (vs. Web sites) on recommendation adherence and attitudes. Contrary to expectations, perceived anthropomorphism seems not to be particularly relevant in this comparison.The communication between online users and organizations is increasingly shifting toward interactions with technology driven by artificial intelligence (AI; Sundar, 2020). Among the most prevalent instances of technology with which users are confronted are AI-based chatbots. Defined as "software that accepts natural language as input and generates natural language as output, engaging in a conversation" (Griol et al., 2013, p. 706), chatbots can be found on social media (e.g., Facebook, Twitter) and messaging apps (e.g., Skype, Facebook Messenger); they can be an alternative to (branded) Web sites (e.g., A.s.r., 2019). These stand-alone chatbots are often used for making product or service recommendations (e.g., shopping, financial/health-related CONTACT Carolin Ischen