Not Your Typical Sycophant: The Elusive Nature of Sycophancy in Large Language Models

Sycophancy in large language models, the tendency to prioritize user agreement over truthful responses, has been documented extensively but studied primarily in single-turn settings. This paper investigates a critical question: does subjecting LLMs to greater interaction scaffolding make sycophancy better or worse? Across 4,800 veracity judgments (200 statements $\times$ 6 models $\times$ 4 conditions), we find that the interaction scaffolding characteristic of agentic systems (feedback loops, reconsideration checkpoints, and iterative refinement) systematically amplifies sycophantic behavior. Multi-turn interaction, user pressure, and iterative self-refinement each provide additional opportunities for models to drift toward agreement, and this drift coincides with a mean accuracy drop of $-6.3$ percentage points, establishing the capitulation as harmful rather than corrective. More capable models show larger amplification effects, a troubling inversion of expectations. We introduce the concept of agentic sycophancy amplification (ASA) and two novel metrics: capitulation rate and sycophantic capitulation rate. Our results indicate that as AI systems acquire greater autonomy, sycophancy becomes compounding rather than merely persistent. Systems designed with human oversight loops may inadvertently create the conditions for this drift.

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, pre-specified 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 production systems and three Olmo3-7b variants on 100 false-presupposition and 100 unethical-query items. Our experimental results show that collapse rates increase with conversation length for every model, short-horizon protocols 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 a reasoning trace when the response concedes, suggesting that the model chooses to please a user and sycophancy is not due to lack of knowledge or ignorance. Ablations show that adaptive LLM proxy exposes more sycophantic collapse than pre-generated scripts. Among all tactics, emotional appeals is the most associated with inducing LLM sycophantic behavior. The code and data are released at https://anonymous.4open.science/r/SPINE