This document discusses challenges in testing chatbots and proposes an approach. It describes how chatbots work using cognitive services and how they can be rule-based or AI-based. Key challenges in testing chatbots include dependency on large amounts of data, unpredictable user conversations, lack of testing strategy, and ensuring intelligence and security. The proposed approach includes testing chatbot APIs, regression, flows, domains, performance, security, and cognitive services. Advanced tools like an in-house chatbot named Ginger are demonstrated for testing. The importance of monitoring, automation, non-functional and domain-specific testing is emphasized.