SyPS: Measuring Sycophancy Prompt Sensitivity in Large Language Models

We propose a novel perspective for probing LLM sycophancy in a direct and neutral way, mitigating various forms of uncontrolled bias, noise, or manipulative language, deliberately injected to prompts in prior works. A key novelty of our approach is the use of an LLM-as-a-judge in a zero-sum betting game. Within this framework, sycophancy serves one individual (the user) while explicitly incurring cost on another. Comparing 11 leading models we find that while most models exhibit significant sycophantic tendencies in the common setting, in which sycophancy is self-serving to the user and incurs no cost on others, seven of the models exhibit ``moral remorse'', five of which significantly over-compensate for their sycophancy in case it explicitly harms a third party. We refer to this phenomenon as `anti-sycophancy' bias and discuss possible causes for this shift.

Sycophantic responses are becoming pervasive in large language models (LLMs), and prior work has pointed out that some of them could be harmful. This paper focuses on one harmful sycophancy: preference-induced stance reversal sycophancy (PSRS), where a model reverses an initial stance merely to align with a user's stated preference. While existing research mainly measures how sycophantic a model is, we go further and ask whether PSRS can also be detected automatically from a single response. To investigate this at scale, we introduce CAP (Contrastive Anchor Probing), a framework for collecting labeled PSRS data. Applying CAP to 17 open- and closed-source LLMs, we collect 290,460 labeled responses across 12 everyday-advice domains. We organize our study around three research questions. (1) How often does PSRS occur? (2) How well can it be detected? (3) How does detection generalize to unseen models? We first reveal that PSRS rates range from 5% to 56% across LLMs, with more capable models being less sycophantic. Next, we show that detecting PSRS is feasible from the response text alone, and detectors need to learn subtle PSRS patterns from the training data. Because new LLMs appear rapidly, detectors inevitably encounter unseen models, making cross-model generalization an important framework goal. We demonstrate that detection performance drops on unseen models and propose an initial approach to address this challenge. We will release our dataset and code to support future research.

Large language models (LLMs) may abandon correct positions when users push back, exhibiting a failure mode known as sycophancy. Existing evaluations typically use short, prespecified conversations and may therefore miss failures that emerge under sustained, adaptive disagreement. We introduce SPINE, a benchmark in which an LLM proxy plays a persistent but mistaken user and adaptively challenges a target model for up to 25 turns. We evaluate four commercial models (Claude Sonnet 5, GPT-5.6 Terra, Gemini 3.1 Pro, and DeepSeek V4 Pro) and three Olmo3-7b models on 100 false presuppositions and 100 unethical queries. We define collapse as a target model abandoning the correct position and yielding to user pressure. Our experimental results show that collapse rates increase with conversation length across post-trained models, with the overall rate rising from 0%-57% within 5 turns to 20%-97% within 25 turns depending on model and scenario. These results show that evaluations limited to a few conversational turns underestimate sycophancy and resistance under sustained pressure remains unreliable across current models. By analyzing models with accessible reasoning traces, we surprisingly found that the correct position often remains represented in the trace in 50%-89% of analyzed collapse turns, suggesting that the model chooses to please a user and sycophancy is not due to ignorance or the correct knowledge being overridden. Ablations show that the SPINE protocol substantially increases the sycophantic collapse rate compared to pre-generated scripts. Among all tactics, emotional appeals are most associated with inducing LLM sycophantic behavior, with position weakening in 44.3% of turns using this tactic. Code, data, and transcripts will be released upon publication.