Generative AI deployments often encounter significant challenges before reaching production, with many projects stalling or being abandoned due to various failure modes. These include hallucination cascades, where AI generates false information, tool invocation misfires causing operational errors, context window truncation leading to incomplete responses, and planner infinite loops that waste resources. Additional issues include data leakage exposing sensitive information, non-deterministic output drift affecting reliability, memory bloat causing performance degradation, latency spikes resulting in resource starvation, emergent multi-agent conflicts, and evaluation blind spots that leave unknown errors unchecked. Solutions involve implementing robust observability and debugging strategies, such as using platforms like Galileo for real-time monitoring, error detection, and continuous learning via human feedback, which help maintain AI agent reliability and prevent failures from occurring in production environments.