SPINE: Measuring LLM Sycophancy under Sustained Multi-Turn Pressure

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.