Single-prompt evaluations dominate current LLM benchmarking, yet they fail to capture the conversational dynamics where real-world harm occurs. In this study, we examined whether conversation length affects response veracity by evaluating LLM performance on the BoolQ dataset under varying length and scaffolding conditions. Our results across three distinct LLMs revealed model-specific vulnerabilities that are invisible under single-turn testing. The length-dependent and scaffold-specific effects we observed demonstrate a fundamental limitation of static evaluations, as deployment-relevant vulnerabilities could only be spotted in a multi-turn conversational setting.