This paper presents research on a multi-turn-to-single-turn (M2S) technique that condenses repetitive red team activities into a single, structured prompt. Unlike previous studies that rely on a few handwritten templates, this paper proposes the X-Teaming Evolutionary M2S framework, which automatically discovers and optimizes M2S templates using a language model (LLM)-based evolutionary algorithm. It uses smart sampling from 12 sources and a StrongREJECT-inspired LLM as a judge, resulting in a fully auditable log. After five evolutionary generations, with a success threshold of 0.70, we achieve an overall success rate of 44.8% (103 out of 230) on two new template families and GPT-4.1. Through 2,500 cross-model evaluations, we demonstrate that structural improvements are transferable, but vary across target models. We find a positive correlation between prompt length and scores, highlighting the importance of length-sensitive judgement. The source code, configuration, and results are available on GitHub.