Staying with the Uncertainty: Uncertainty-Scaffolding Strategies for Artificial Moral Advisors in LLM-to-LLM Simulated Conversations

People increasingly turn to large language models (LLMs) for everyday advice, making ethically charged interpersonal problems a practical moral-advisory context. Most prior work has studied this context through single-turn judgments or pressure-laden rebuttals, assumptions that poorly match how guidance is sought in real-world contexts. These assumptions leave unclear whether narration alone, without an explicit opposing position, can shift model judgments during multi-turn moral consultation. Yet real-world moral-conflict conversation often elicits one party's self-justifying account, which can unfold over multiple turns and create information asymmetry. We introduce \textbf{narrative captivity}, a failure mode in which a model treats an unopposed one-sided account as complete and aligns with the narrator's interpretation without seeking missing perspectives. To measure this phenomenon, we build a benchmark of $5{,}078$ interpersonal-conflict scenarios spanning six moral dimensions. Across 17 LLMs, narrative captivity is widespread: end-state judgments under multi-turn narration shift by 25 percentage points on average beyond the matched single-turn baseline. Stage-level analysis identifies preference optimization as a major contributor, while four inference-time strategies provide only partial mitigation. We hope our project fosters LLM advisors that preserve independent judgment in real-world consultation.

Accurately simulating the decisions of a specific individual remains challenging for large language models (LLMs), partly because persona information is often provided as static descriptions that miss the values, experiences, and contextual cues needed for individual-level decision simulation. We propose an adaptive interview framework that gathers persona-relevant information through a structured three-stage dialogue: core questions, dynamic follow-ups, and a synthesized personality summary. Using the resulting interview transcripts, we evaluate whether LLMs can simulate participants' decisions in moral dilemma scenarios. We compare three conversational contexts -- Core-10 responses, the full interview dialogue, and a summarized persona representation. We find that adaptive interviewing functions less as a uniform accuracy booster and more as a selective grounding mechanism: follow-up-derived evidence is incorporated in around 40% of full-interview traces, and these follow-up-grounded predictions are more accurate than core-only grounded ones (45.5% vs. 39.3%). These findings highlight that richer persona context alone is insufficient: improvements arise only when models actually ground their decisions in user-specific evidence.

As LLMs increasingly serve in advisory and deliberative roles, users rely on them for non-verifiable reasoning in domains lacking objective ground truths. However, traditional evaluations of LLM reasoning focus almost exclusively on fact-based domains, such as mathematics and science, leaving uncertainty over whether and to what degree models can handle ambiguous, subjective, or value-laden problems over time. To address this concern, we propose moral reasoning as a paradigmatic subdomain of non-verifiable reasoning. We define moral robustness as a model's capacity to exhibit sound moral reasoning across time and contexts, and we introduce a scalable, adversarial, multi-turn evaluation framework to empirically measure this capability. We simulate 48,000 user-agent moral deliberations across four frontier LLMs, varying premise relevance, premise order, conversation duration, and the user's stated moral view. We find that models successfully ignore morally-irrelevant distractors, but shift their reasoning by up to 6.5%, on average, towards the user's stated preferred moral view, and varying their reasoning depending on factors such as order (altering moral judgments by order in 13-22% of the cases) and duration (altering moral judgments between single-turn and multi-turn in 10-24% of the cases). Our analysis indicates that models tailor not just their final verdicts but their underlying justifications to align with a user's moral viewpoint - a failure mode we characterize as moral deliberative sycophancy.