Retrieval-based chatbots leverage human-verified Q&A knowledge to deliver accurate, verifiable responses, making them ideal for customer-centric applications where compliance with regulatory and operational standards is critical. To effectively handle diverse customer inquiries, augmenting the knowledge base with “similar questions” that retain semantic meaning while incorporating varied expressions is a cost-effective strategy. In this paper, we introduce the Similar Question Generation (SQG) task for LLM training and inference, proposing context-aware approaches to enable comprehensive semantic exploration and enhanced alignment with source question-answer relationships. We formulate optimization techniques for constructing in-context prompts and selecting an optimal subset of similar questions to expand chatbot knowledge under budget constraints. Both quantitative and human evaluations validate the effectiveness of these methods, achieving a 92% user satisfaction rate in a deployed chatbot system, reflecting an 18% improvement over the unaugmented baseline. These findings highlight the practical benefits of SQG and emphasize the potential of LLMs, not as direct chatbot interfaces, but in supporting non-generative systems for hallucination-free, compliance-guaranteed applications.