Building an AI-powered course recommendation chatbot sounds simple—until you face real-world limitations. Our journey with DigitalOcean Gradient AI reveals the ups and downs of using prebuilt templates, configuring RAG, and managing multilingual data. We document how different LLMs (Llama 3.1, 3.3, and DeepSeek-R1) performed, what guardrails did—and didn’t—solve, and how Hubert, our assistant, evolved. If you’re new to AI agents and want candid lessons before launching your own, you’ll find plenty of practical takeaways in our story.