In the digital age, cultural organizations strive to retain audience engagement especially via experimentation with novel technologies and social media. The latter are increasingly influencing the way cultural heritage is perceived, providing options for grappling with crucial issues in the sector, including sustainability, openness, and public participation. One tool that has been deployed to explore these issues is the chatbot, a computer program designed to simulate conversation with human users, especially over the internet. Chatbots run through different conversational interfaces, but they have a particularly heavy application in Facebook Messenger. Within the museums and cultural sector specifically, these robotic media are regularly proclaimed to offer novel engagement mechanisms that can empower participants to actively participate in the heritage process. However, most heritage Messenger bots are purely informative and object- or exhibit-centered, providing little opportunity for meaningful interactivity, creative expression, or critical engagement. This article explores and critically reviews three Messenger chatbots related to heritage organizations, concluding with suggestions for their future development.