# Breakdowns in Conversational AI: Interactional Failures in Emotionally and Ethically Sensitive Contexts

arXiv: https://arxiv.org/abs/2604.02713 · HTML: https://mlsanity.com/paper/2604.02713/

## Key facts

- No citing papers in the map yet (data through 14 Oct 2026).
- Builds on 32 of its 52 references that are in the map.
- First posted on arXiv 3 Apr 2026.

## Builds on (most cited first, 30 of 32)

- [Training language models to follow instructions with human feedback](https://mlsanity.com/paper/2203.02155/) (2022)
- [Judging LLM-as-a-Judge with MT-Bench and Chatbot Arena](https://mlsanity.com/paper/2306.05685/) (2023)
- [GPT-4o System Card](https://mlsanity.com/paper/2410.21276/) (2024)
- [Finetuned Language Models Are Zero-Shot Learners](https://mlsanity.com/paper/2109.01652/) (2021)
- [Training a Helpful and Harmless Assistant with Reinforcement Learning from Human Feedback](https://mlsanity.com/paper/2204.05862/) (2022)
- [Constitutional AI: Harmlessness from AI Feedback](https://mlsanity.com/paper/2212.08073/) (2022)
- [A Diversity-Promoting Objective Function for Neural Conversation Models](https://mlsanity.com/paper/1510.03055/) (2015)
- [Red Teaming Language Models with Language Models](https://mlsanity.com/paper/2202.03286/) (2022)
- [DialoGPT: Large-Scale Generative Pre-training for Conversational Response Generation](https://mlsanity.com/paper/1911.00536/) (2019)
- [Recipes for building an open-domain chatbot](https://mlsanity.com/paper/2004.13637/) (2020)
- [JudgeLM: Fine-tuned Large Language Models are Scalable Judges](https://mlsanity.com/paper/2310.17631/) (2023)
- [How NOT To Evaluate Your Dialogue System: An Empirical Study of Unsupervised Evaluation Metrics for Dialogue Response Generation](https://mlsanity.com/paper/1603.08023/) (2016)
- [Towards Emotional Support Dialog Systems](https://mlsanity.com/paper/2106.01144/) (2021)
- [SODA: Million-scale Dialogue Distillation with Social Commonsense Contextualization](https://mlsanity.com/paper/2212.10465/) (2022)
- [Generating Informative and Diverse Conversational Responses via Adversarial Information Maximization](https://mlsanity.com/paper/1809.05972/) (2018)
- [SoulChat: Improving LLMs' Empathy, Listening, and Comfort Abilities through Fine-tuning with Multi-turn Empathy Conversations](https://mlsanity.com/paper/2311.00273/) (2023)
- [ProsocialDialog: A Prosocial Backbone for Conversational Agents](https://mlsanity.com/paper/2205.12688/) (2022)
- [From Eliza to XiaoIce: Challenges and Opportunities with Social Chatbots](https://mlsanity.com/paper/1801.01957/) (2018)
- [EQ-Bench: An Emotional Intelligence Benchmark for Large Language Models](https://mlsanity.com/paper/2312.06281/) (2023)
- [Expressing stigma and inappropriate responses prevents LLMs from safely replacing mental health providers](https://mlsanity.com/paper/2504.18412/) (2025)
- [Human-AI Collaboration Enables More Empathic Conversations in Text-based Peer-to-Peer Mental Health Support](https://mlsanity.com/paper/2203.15144/) (2022)
- [A Computational Framework for Behavioral Assessment of LLM Therapists](https://mlsanity.com/paper/2401.00820/) (2024)
- [A User Simulator for Task-Completion Dialogues](https://mlsanity.com/paper/1612.05688/) (2016)
- [From Lived Experience to Insight: Unpacking the Psychological Risks of Using AI Conversational Agents](https://mlsanity.com/paper/2412.07951/) (2024)
- [ESC-Eval: Evaluating Emotion Support Conversations in Large Language Models](https://mlsanity.com/paper/2406.14952/) (2024)
- [SPHERE: An Evaluation Card for Human-AI Systems](https://mlsanity.com/paper/2504.07971/) (2025)
- [ESC-Judge: A Framework for Comparing Emotional Support Conversational Agents](https://mlsanity.com/paper/2505.12531/) (2025)
- [Better Slow than Sorry: Introducing Positive Friction for Reliable Dialogue Systems](https://mlsanity.com/paper/2501.17348/) (2025)
- [LLM Content Moderation and User Satisfaction: Evidence from Response Refusals in Chatbot Arena](https://mlsanity.com/paper/2501.03266/) (2025)
- [Tailored Emotional LLM-Supporter: Enhancing Cultural Sensitivity](https://mlsanity.com/paper/2508.07902/) (2025)

## Abstract (arXiv)

Conversational AI is increasingly deployed in emotionally charged and ethically sensitive interactions. Previous research has primarily concentrated on emotional benchmarks or static safety checks, overlooking how alignment unfolds in evolving conversation. We explore the research question: what breakdowns arise when conversational agents confront emotionally and ethically sensitive behaviors, and how do these affect dialogue quality? To stress-test chatbot performance, we develop a persona-conditioned user simulator capable of engaging in multi-turn dialogue with psychological personas and staged emotional pacing. Our analysis reveals that mainstream models exhibit recurrent breakdowns that intensify as emotional trajectories escalate. We identify several common failure patterns, including affective misalignments, ethical guidance failures, and cross-dimensional trade-offs where empathy supersedes or undermines responsibility. We organize these patterns into a taxonomy and discuss the design implications, highlighting the necessity to maintain ethical coherence and affective sensitivity throughout dynamic interactions. The study offers the HCI community a new perspective on the diagnosis and improvement of conversational AI in value-sensitive and emotionally charged contexts.