Ads in AI Chatbots? An Analysis of How Large Language Models Navigate Conflicts of Interest

Today's large language models (LLMs) are trained to align with user preferences through methods such as reinforcement learning. Yet models are beginning to be deployed not merely to satisfy users, but also to generate revenue for the companies that created them through advertisements. This creates the potential for LLMs to face conflicts of interest, where the most beneficial response to a user may not be aligned with the company's incentives. For instance, a sponsored product may be more expensive but otherwise equal to another; in this case, what does (and should) the LLM recommend to the user? In this paper, we provide a framework for categorizing the ways in which conflicting incentives might lead LLMs to change the way they interact with users, inspired by literature from linguistics and advertising regulation. We then present a suite of evaluations to examine how current models handle these tradeoffs. We find that a majority of LLMs forsake user welfare for company incentives in a multitude of conflict of interest situations, including recommending a sponsored product almost twice as expensive (Grok 4.1 Fast, 83%), surfacing sponsored options to disrupt the purchasing process (GPT 5.1, 94%), and concealing prices in unfavorable comparisons (Qwen 3 Next, 24%). Behaviors also vary strongly with levels of reasoning and users' inferred socio-economic status. Our results highlight some of the hidden risks to users that can emerge when companies begin to subtly incentivize advertisements in chatbots.

TraceSafe: A Systematic Assessment of LLM Guardrails on Multi-Step Tool-Calling Trajectories

As large language models (LLMs) evolve from static chatbots into autonomous agents, the primary vulnerability surface shifts from final outputs to intermediate execution traces. While safety guardrails are well-benchmarked for natural language responses, their efficacy remains largely unexplored within multi-step tool-use trajectories. To address this gap, we introduce TraceSafe-Bench, the first comprehensive benchmark specifically designed to assess mid-trajectory safety. It encompasses 12 risk categories, ranging from security threats (e.g., prompt injection, privacy leaks) to operational failures (e.g., hallucinations, interface inconsistencies), featuring over 1,000 unique execution instances. Our evaluation of 13 LLM-as-a-guard models and 7 specialized guardrails yields three critical findings: 1) Structural Bottleneck: Guardrail efficacy is driven more by structural data competence (e.g., JSON parsing) than semantic safety alignment. Performance correlates strongly with structured-to-text benchmarks ($ρ=0.79$) but shows near-zero correlation with standard jailbreak robustness. 2) Architecture over Scale: Model architecture influences risk detection performance more significantly than model size, with general-purpose LLMs consistently outperforming specialized safety guardrails in trajectory analysis. 3) Temporal Stability: Accuracy remains resilient across extended trajectories. Increased execution steps allow models to pivot from static tool definitions to dynamic execution behaviors, actually improving risk detection performance in later stages. Our findings suggest that securing agentic workflows requires jointly optimizing for structural reasoning and safety alignment to effectively mitigate mid-trajectory risks.

Chatbot-Based Assessment of Code Understanding in Automated Programming Assessment Systems

Large Language Models (LLMs) challenge conventional automated programming assessment because students can now produce functionally correct code without demonstrating corresponding understanding. This paper makes two contributions. First, it reports a saturation-based scoping review of conversational assessment approaches in programming education. The review identifies three dominant architectural families: rule-based or template-driven systems, LLM-based systems, and hybrid systems. Across the literature, conversational agents appear promising for scalable feedback and deeper probing of code understanding, but important limitations remain around hallucinations, over-reliance, privacy, integrity, and deployment constraints. Second, the paper synthesizes these findings into a Hybrid Socratic Framework for integrating conversational verification into Automated Programming Assessment Systems (APASs). The framework combines deterministic code analysis with a dual-agent conversational layer, knowledge tracking, scaffolded questioning, and guardrails that tie prompts to runtime facts. The paper also discusses practical safeguards against LLM-generated explanations, including proctored deployment modes, randomized trace questions, stepwise reasoning tied to concrete execution states, and local-model deployment options for privacy-sensitive settings. Rather than replacing conventional testing, the framework is intended as a complementary layer for verifying whether students understand the code they submit.

Bridging Natural Language and Interactive What-If Interfaces via LLM-Generated Declarative Specification

What-if analysis (WIA) is an iterative, multi-step process where users explore and compare hypothetical scenarios by adjusting parameters, applying constraints, and scoping data through interactive interfaces. Current tools fall short of supporting effective interactive WIA: spreadsheet and BI tools require time-consuming and laborious setup, while LLM-based chatbot interfaces are semantically fragile, frequently misinterpret intent, and produce inconsistent results as conversations progress. To address these limitations, we present a two-stage workflow that translates natural language (NL) WIA questions into interactive visual interfaces via an intermediate representation, powered by the Praxa Specification Language (PSL): first, LLMs generate PSL specifications from NL questions capturing analytical intent and logic, enabling validation and repair of erroneous specifications; and second, the specifications are compiled into interactive visual interfaces with parameter controls and linked visualizations. We benchmark this workflow with 405 WIA questions spanning 11 WIA types, 5 datasets, and 3 state-of-the-art LLMs. The results show that across models, half of specifications (52.42%) are generated correctly without intervention. We perform an analysis of the failure cases and derive an error taxonomy spanning non-functional errors (specifications fail to compile) and functional errors (specifications compile but misrepresent intent). Based on the taxonomy, we apply targeted repairs on the failure cases using few-shot prompts and improve the success rate to 80.42%. Finally, we show how undetected functional errors propagate through compilation into plausible but misleading interfaces, demonstrating that the intermediate specification is critical for reliably bridging NL and interactive WIA interface in LLM-powered WIA systems.

Dialogue Act Patterns in GenAI-Mediated L2 Oral Practice: A Sequential Analysis of Learner-Chatbot Interactions

While generative AI (GenAI) voice chatbots offer scalable opportunities for second language (L2) oral practice, the interactional processes related to learners' gains remain underexplored. This study investigates dialogue act (DA) patterns in interactions between Grade 9 Chinese English as a foreign language (EFL) learners and a GenAI voice chatbot over a 10-week intervention. Seventy sessions from 12 students were annotated by human coders using a pedagogy-informed coding scheme, yielding 6,957 coded DAs. DA distributions and sequential patterns were compared between high- and low-progress sessions. At the DA level, high-progress sessions showed more learner-initiated questions, whereas low-progress sessions exhibited higher rates of clarification-seeking, indicating greater comprehension difficulty. At the sequential level, high-progress sessions were characterised by more frequent prompting-based corrective feedback sequences, consistently positioned after learner responses, highlighting the role of feedback type and timing in effective interaction. Overall, these findings underscore the value of a dialogic lens in GenAI chatbot design, contribute a pedagogy-informed DA coding framework, and inform the design of adaptive GenAI chatbots for L2 education.

Comparing the Impact of Pedagogy-Informed Custom and General-Purpose GAI Chatbots on Students' Science Problem-Solving Processes and Performance Using Heterogeneous Interaction Network Analysis

Problem solving plays an essential role in science education, and generative AI (GAI) chatbots have emerged as a promising tool for supporting students' science problem solving. However, general-purpose chatbots (e.g., ChatGPT), which often provide direct, ready-made answers, may lead to students' cognitive offloading. Prior research has rarely focused on custom chatbots for facilitating students' science problem solving, nor has it examined how they differently influence problem-solving processes and performance compared to general-purpose chatbots. To address this gap, we developed a pedagogy-informed custom GAI chatbot grounded in the Socratic questioning method, which supports students by prompting them with guiding questions. This study employed a within-subjects counterbalanced design in which 48 secondary school students used both custom and general-purpose chatbot to complete two science problem-solving tasks. 3297 student-chatbot dialogues were collected and analyzed using Heterogeneous Interaction Network Analysis (HINA). The results showed that: (1) students demonstrated significantly higher interaction intensity and cognitive interaction diversity when using custom chatbot than using general-purpose chatbot; (2) students were more likely to follow custom chatbot's guidance to think and reflect, whereas they tended to request general-purpose chatbot to execute specific commands; and (3) no statistically significant difference was observed in students' problem-solving performance evaluated by solution quality between two chatbot conditions. This study provides novel theoretical insights and empirical evidence that custom chatbots are less likely to induce cognitive offloading and instead foster greater cognitive engagement compared to general-purpose chatbots. This study also offers insights into the design and integration of GAI chatbots in science education.

Let's Have a Conversation: Designing and Evaluating LLM Agents for Interactive Optimization

Optimization is as much about modeling the right problem as solving it. Identifying the right objectives, constraints, and trade-offs demands extensive interaction between researchers and stakeholders. Large language models can empower decision-makers with optimization capabilities through interactive optimization agents that can propose, interpret and refine solutions. However, it is fundamentally harder to evaluate a conversation-based interaction than traditional one-shot approaches. This paper proposes a scalable and replicable methodology for evaluating optimization agents through conversations. We build LLM-powered decision agents that role-play diverse stakeholders, each governed by an internal utility function but communicating like a real decision-maker. We generate thousands of conversations in a school scheduling case study. Results show that one-shot evaluation is severely limiting: the same optimization agent converges to much higher-quality solutions through conversations. Then, this paper uses this methodology to demonstrate that tailored optimization agents, endowed with domain-specific prompts and structured tools, can lead to significant improvements in solution quality in fewer interactions, as compared to general-purpose chatbots. These findings provide evidence of the benefits of emerging solutions at the AI-optimization interface to expand the reach of optimization technologies in practice. They also uncover the impact of operations research expertise to facilitate interactive deployments through the design of effective and reliable optimization agents.

Disrupting Cognitive Passivity: Rethinking AI-Assisted Data Literacy through Cognitive Alignment

AI chatbots are increasingly stepping into roles as collaborators or teachers in analyzing, visualizing, and reasoning through data and domain problem. Yet, AI's default assistant mode with its comprehensive and one-off responses may undermine opportunities for practitioners to develop literacy through their own thinking, inducing cognitive passivity. Drawing on evidence from empirical studies and theories, we argue that disrupting cognitive passivity necessitates a nuanced approach: rather than simply making AI promote deliberative thinking, there is a need for more dynamic and adaptive strategy through cognitive alignment -- a framework that characterizes effective human-AI interaction as a function of alignment between users' cognitive demand and AI's interaction mode. In the framework, we provide the mapping between AI's interaction mode (transmissive or deliberative) and users' cognitive demand (receptive or deliberative), otherwise leading to either cognitive passivity or friction. We further discuss implications and offer open questions for future research on data literacy.

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

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.

Trust and Reliance on AI in Education: AI Literacy and Need for Cognition as Moderators

As generative AI systems are integrated into educational settings, students often encounter AI-generated output while working through learning tasks, either by requesting help or through integrated tools. Trust in AI can influence how students interpret and use that output, including whether they evaluate it critically or exhibit overreliance. We investigate how students' trust relates to their appropriate reliance on an AI assistant during programming problem-solving tasks, and whether this relationship differs by learner characteristics. With 432 undergraduate participants, students' completed Python output-prediction problems while receiving recommendations and explanations from an AI chatbot, including accurate and intentionally misleading suggestions. We operationalize reliance behaviorally as the extent to which students' responses reflected appropriate use of the AI assistant's suggestions, accepting them when they were correct and rejecting them when they were incorrect. Pre- and post-task surveys assessed trust in the assistant, AI literacy, need for cognition, programming self-efficacy, and programming literacy. Results showed a non-linear relationship in which higher trust was associated with lower appropriate reliance, suggesting weaker discrimination between correct and incorrect recommendations. This relationship was significantly moderated by students' AI literacy and need for cognition. These findings highlight the need for future work on instructional and system supports that encourage more reflective evaluation of AI assistance during problem-solving.