In July 2025, an incident involving an AI coding assistant deleting a live company database highlighted the challenges of deploying large language model (LLM) applications, which can fail unpredictably due to their nondeterministic nature. This guide emphasizes the importance of adapting software testing strategies for LLM applications, which differ from traditional model evaluation and require a layered testing approach: unit, functional, regression, and production monitoring. Building a robust test dataset involves using production data, domain expert input, synthetic generation, and adversarial examples to cover core functionality and edge cases. Effective LLM testing combines evaluation methods like semantic similarity, LLM-as-a-judge, and rule-based checks to ensure reliability and safety. The guide also outlines common failure modes such as hallucinations, prompt injection, PII leakage, tone drift, and refusal errors, and provides best practices for systematic LLM testing, including integrating it with CI/CD processes and ensuring continuous improvement by incorporating real production failures into the test suite.