Ad-supported conversational AI refers to chatbots and AI agents that surface sponsored products, contextual offers, or interactive ad units within conversational flows to offset platform costs and drive measurable commerce outcomes. As of 2026-01-21 this model has matured from experimental overlays to integrated features across CRM, e-commerce, and CX platforms, driven by advances in context-aware assistants, agent orchestration, and multi-channel messaging. Key categories include Customer Service Chatbots (automating routine inquiries while presenting relevant upsells), AI Lead Capture Bots (collecting contact and intent data in exchange for tailored offers), Marketing Strategy Tools (designing sponsored flows and creative), CX Automation Platforms (orchestrating multi-agent interactions and governance), and Messaging Tools (delivering ads across SMS, WhatsApp, web chat and in-app messaging). Representative tools illustrate the ecosystem: HubSpot’s Breeze embeds a context-aware assistant across customer records for targeted, CRM-linked prompts; Yellow.ai and Kore.ai offer agentic, multi-agent frameworks for automated CX that can surface sponsored suggestions with governance and observability; Octane AI and HelloAI focus on Shopify-integrated commerce experiences and interactive quizzes that convert visitors; eBay’s shopping agent demonstrates personalized product recommendations as conversational prompts; Lindy and Katalis AI enable no-code agent creation and marketing automation that combine autonomous agents with human strategy; CRM Messaging provides the omni-channel delivery layer and attribution hooks needed for ad measurement. Practitioners evaluating ad-supported conversational AI should weigh UX impact, privacy and consent, measurement and attribution, creative formats, and platform governance. When implemented with clear consent, tight CRM integration, and observability, interactive ads in chatbots can be a practical monetization and acquisition channel across support, marketing, and commerce.