In this talk, I will present a systematic evaluation of large language models (LLMs) in multi-turn conversational settings, focusing on the “lost-in-conversation” phenomenon. I will introduce a novel benchmarking methodology that transforms single-turn tasks into multi-turn interactions using a simulated user and classifier-based evaluation pipeline. Through large-scale simulations across diverse tasks, I will demonstrate that LLMs often fail to recover from early misinterpretations, exhibit high unreliability, and produce verbose or bloated responses. I will also discuss the limitations of current mitigation strategies such as agent-based concatenation and temperature tuning, and highlight the implications for future LLM design and evaluation.