Fine-grained image-caption alignment is crucial for vision-language models (VLMs), especially in socially critical contexts such as identifying real-world risk scenarios or distinguishing cultural proxies, where correct interpretation hinges on subtle visual or linguistic clues and where minor misinterpretations can lead to significant real-world consequences. We present MiSCHiEF, a set of two benchmarking datasets (MiC and MiS) based on a contrastive pair design in the domains of safety and culture, and evaluate four VLMs on tasks requiring fine-grained differentiation of paired images and captions. In both datasets, each sample contains two minimally differing captions and corresponding minimally differing images. In MiS, the image-caption pairs depict a safe and an unsafe scenario, while in MiC, they depict cultural proxies in two distinct cultural contexts. We find that models generally perform better at confirming the correct image-caption pair than rejecting incorrect ones. Additionally, models achieve higher accuracy when selecting the correct caption from two highly similar captions for a given image, compared to the converse task. The results, overall, highlight persistent modality misalignment challenges in current VLMs, underscoring the difficulty of precise cross-modal grounding required for applications with subtle semantic and visual distinctions.

Large Language Models (LLMs) are increasingly integrated into high-stakes applications, making robust safety guarantees a central practical and commercial concern. Existing safety evaluations predominantly rely on fixed collections of harmful prompts, implicitly assuming non-adaptive adversaries and thereby overlooking realistic attack scenarios in which inputs are iteratively refined to evade safeguards. In this work, we examine the vulnerability of contemporary language models to automated, adversarial prompt refinement. We repurpose black-box prompt optimization techniques, originally designed to improve performance on benign tasks, to systematically search for safety failures. Using DSPy, we apply three such optimizers to prompts drawn from HarmfulQA and JailbreakBench, explicitly optimizing toward a continuous danger score in the range 0 to 1 provided by an independent evaluator model (GPT-5.1). Our results demonstrate a substantial reduction in effective safety safeguards, with the effects being especially pronounced for open-source small language models. For example, the average danger score of Qwen 3 8B increases from 0.09 in its baseline setting to 0.79 after optimization. These findings suggest that static benchmarks may underestimate residual risk, indicating that automated, adaptive red-teaming is a necessary component of robust safety evaluation.

Reinforcement learning from human feedback (RLHF) has emerged as the primary method for aligning large language models (LLMs) with human preferences. While it enables LLMs to achieve human-level alignment, it often incurs significant computational and financial costs due to its reliance on training external reward models or human-labeled preferences. In this work, we propose Implicit Preference Optimization (IPO), an alternative approach that leverages generative LLMs as preference classifiers, thereby reducing the dependence on external human feedback or reward models to obtain preferences. We conduct a comprehensive evaluation on the preference classification ability of LLMs using RewardBench, assessing models across different sizes, architectures, and training levels to validate our hypothesis. Furthermore, we investigate the self-improvement capabilities of LLMs by generating multiple responses for a given instruction and employing the model itself as a preference classifier for Direct Preference Optimization (DPO)-based training. Our findings demonstrate that models trained through IPO achieve performance comparable to those utilizing state-of-the-art reward models for obtaining preferences.