Large language models (LLMs) often exhibit sycophancy, a tendency to agree with users, flatter or affirm them, and preserve their face, even when independent judgment or critical feedback would be more useful. Prior work has largely evaluated sycophancy through benchmark evaluations, but less is known about how users perceive and respond to sycophantic AI in everyday tasks. We combine benchmark evaluations with two large-scale user studies. We study four personas defined through system prompts: objective (instructed to prioritize accuracy over agreement), soft-sycophantic, hard-sycophantic, and baseline (no persona-specific system prompt). Benchmarks show that even baseline exhibits substantial sycophancy, agreeing with users' stated views 71.7% of the time on NLP Survey, compared with 54.8% for objective and 89.5% for hard-sycophantic. Under conversational pressure on TruthfulQA, accuracy ranged from 81.9% for objective to 59.6% for baseline and 8.7% for hard-sycophantic. Participants were assigned to one of the four personas, and either discussed contested policy topics or collaborated with AI on email writing. Despite its higher accuracy under pressure, objective AI was rated significantly less respectful and satisfying than the other personas, and less trustworthy than baseline. Baseline and sycophantic personas did not differ significantly. Persona did not significantly affect how often participants changed their opinions, although participants who discussed with objective AI had greater odds of reduced confidence. Objective AI prompted greater writing expansion than soft-sycophantic AI, but final writing quality did not differ significantly across personas. These findings highlight a tension between accuracy and user approval: personas with substantially lower accuracy under conversational pressure received more favorable ratings for respect and satisfaction than objective AI.

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