Designing deployable and resilient network topologies from natural language requirements remains a challenging problem in network automation. This work investigates the ability of Large Language Models (LLMs) to generate structurally valid and constraint-compliant network topologies through a constraint-driven pipeline combining hierarchical modeling and systematic validation. The framework is evaluated via a multimodel comparison of proprietary and open-weight LLMs across four realistic network scenarios released as a public dataset. We assess structural correctness using node and edge F1-scores against reference topologies, and evaluate resilience through server and content connectivity metrics. In addition, we analyze common failure modes, including interface mismatches and directional inconsistencies in generated topologies. Overall, this work provides a systematic benchmark for understanding how LLMs handle structural and resilience constraints in topology synthesis, and supports informed model selection for AI-driven network design.

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