Despite advances in safety alignment, prompt-rewriting attacks such as persona modulation, fictional framing and persuasion-based reformulation, can bypass safety filters even on frontier models. Existing defenses either rely on non-scalable human curation or white-box optimisation that overfits to specific model internals, leaving aligned models brittle against the very class of adaptive black-box adversaries they will face in deployment. To address this gap, we introduce CHASE (Co-evolutionary Hardening through Adversarial Safety-Escalation), a closed-loop red-blue teaming framework in which a black-box attacker and a safety-aligned defender co-evolve. The attacker is trained via Group Relative Policy Optimization (GRPO) under a multiplicative reward that jointly enforces bypass effectiveness and intent fidelity, while the defender is hardened on the harvested adversarial rewrites through a two-stage GRPO + rejection-sampled SFT pipeline balanced with benign data. Evaluated on BeaverTails and JailbreakBench against five held-out attack families (PAIR, TAP, AutoDAN, PAP, Translation), CHASE cuts mean StrongREJECT score by 43.2% on Llama-3.1-8B-Instruct with 0% false refusal on benign (Alpaca) prompts, at a measured helpfulness cost of a 55.6% refusal rate on XSTest safe prompts and a 1.92-point MT-Bench reduction. A controlled ablation that varies only the training attack distribution shows that this generalisation comes from the template-free attack distribution rather than the pipeline, and the result replicates on Qwen2.5-7B-Instruct. Across the two similarly sized open models we study, these results suggest that template-free RL exploration recovers latent attack primitives that transfer across mechanistically distinct attack families.

Sarcasm is a challenge to sentiment analysis because of the incongruity between stated and implied sentiment. The challenge is exacerbated when the implication may be relevant to a specific country or geographical region. Pragmatic metacognitive prompting (PMP) is a cognition-inspired technique that has been used for pragmatic reasoning. In this paper, we harness PMP for explainable sarcasm detection for Australian and Indian English, alongside a benchmark dataset for standard English. We manually add sarcasm explanations to an existing sarcasm-labeled dataset for Australian and Indian English called BESSTIE, and compare the performance for explainable sarcasm detection for them with FLUTE, a standard English dataset containing sarcasm explanations. Our approach utilising PMP when evaluated on two open-weight LLMs (GEMMA and LLAMA) achieves statistically significant performance improvement across all tasks and datasets when compared with four alternative prompting strategies. We also find that alternative techniques such as agentic prompting mitigate context-related failures by enabling external knowledge retrieval. The focused contribution of our work is utilising PMP in generating sarcasm explanations for varieties of English.