We present, to our knowledge, the most comprehensive cross-model evaluation of LLM agents on offensive cybersecurity tasks, benchmarking 10 frontier models from 7 providers on all 200 challenges of the NYU CTF Bench. Building on the D-CIPHER multi-agent framework, we extend it with multi-provider backend support, a custom Kali Linux environment with over 100 pre-installed penetration testing tools, and runtime tool-discovery agents. Through a controlled factorial study, we find that the Kali Linux environment yields a +9.5 percentage-point improvement over Ubuntu, while auto-prompting and category-specific tips often degrade performance in well-equipped environments. Among models, Claude 4.5 Opus achieves the highest solve rate (59%), followed by Gemini 3 Pro (52%), with Gemini 3 Flash offering the best cost-efficiency at $0.05 per solve. Asymmetric planner/executor model assignments provide no meaningful benefit while coherent same-model configurations consistently outperform mixed-tier pairings. Our results indicate that environment tooling and model selection emerge as the strongest drivers of performance, whereas prompt engineering interventions show diminishing or negative returns in well-equipped environments. Reported performance reflects both model reasoning ability and compatibility with agent tooling and API integration.

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