cs.AIMay 15, 2026

PRISM: Prompt Reliability via Iterative Simulation and Monitoring for Enterprise Conversational AI

Authors: Keshava Chaitanya, Jahnavi Gundakaram

Abstract

Deploying large language model (LLM)-driven conversational agents in enterprise settings requires prompts that are simultaneously correct at launch and resilient to the non-deterministic behavioral drift that characterizes production LLM deployments. Existing prompt optimization frameworks address prompt quality as a one-time compile-time problem, leaving open the equally critical question of how to detect and repair prompt regressions caused by silent LLM behavior changes over time. We present PRISM (Prompt Reliability via Iterative Simulation and Monitoring), a closed-loop framework that treats prompt engineering as a continuous reliability engineering problem rather than a one-time authorship task. PRISM takes as input plain-language agent requirements, a set of configured tools and memory variables, and an initial draft prompt. It automatically generates test cases from requirements, simulates full multi-turn conversations against a platform-faithful LLM environment, evaluates pass/fail using an LLM-as-judge, diagnoses root causes of failures, and surgically repairs the prompt -- iterating until all tests pass. Critically, PRISM is designed to run on a scheduled basis (daily), treating LLM behavioral drift as a first-class reliability concern. We evaluate PRISM across 35 enterprise conversational agents over a three-week deployment period on the Yellow.ai V3 platform. PRISM reduces median prompt authoring time from 2 days to under 30 minutes, achieves 99% production reliability across all evaluated agents, and successfully identifies and repairs production regressions caused by LLM behavioral drift within a 24-hour detection window. Our results suggest that continuous, simulation-driven prompt optimization is both tractable and necessary for reliable enterprise conversational AI at scale.

Explore similar work

CardsList
Sep 4, 2026cs.AI

Beyond Prompts: Measuring and Optimizing LLM Tool-Agent Harnesses

LLM tool agents can be improved without retraining by modifying the runtime harness around a fixed model: prompts, tool interfaces, middleware, state handling, and recovery logic. We study this setting as resource-bounded harness selection for fixed-model multi-turn tool agents, with the search surface scoped to prompts and tool-boundary middleware: edits are guarded intercepts at the tool boundary, not arbitrary rewriting of agent execution logic. Our optimizer-agnostic protocol reports mean held-out lift, worst-condition lift, repeatability, logged cost diagnostics, and RelLift95(B), a conservative estimate of the held-out gain of the harness selected under budget B. We instantiate the protocol with prompt-only and prompt-plus-middleware optimizers, including PRISM, which clusters failures and routes repairs to prompt, tool-boundary middleware, or joint edit surfaces within a Pareto search. On BFCL multi-round, tau2-Retail, and tau2-Telecom, PRISM obtains mean held-out lifts of 14.2, 14.9, and 10.1 percentage points and positive empirical RelLift95 on all three benchmarks, and a component ablation attributes the margin chiefly to failure-surface routing and the edit-pattern constraint. Across optimizers, the results show that some search procedures can occasionally find large gains but still choose brittle updates, so the reliability of the chosen harness should be reported alongside average held-out lift.
Cen Mia Zhao, Haibo Ruan, Wenjie Chen +3
Multi-Turn Tool-Use AgentLarge Language Model AgentsPrompt Engineering
AskPDF
Jun 29, 2026cs.AI

Contrastive Reflection for Iterative Prompt Optimization

LLM agents are becoming central to information retrieval: they issue retrieval queries, synthesize answers, and increasingly serve as judges for IR evaluation. Improving the prompts that control these agents is an optimization problem, but in applied IR settings it often looks less like blind search and more like debugging. Engineers need to know which behavior failed, which nearby behavior still worked, what distinguishes the two, and whether a prompt edit improves held-out quality without introducing regressions. We present Contrastive Reflection, an iterative prompt-optimization framework for agentic IR workflows. The framework starts from a task-centric quality definition: QA agents expose retrieval or reasoning traces, and grading agents expose dimension-level scores and rationales. These structured traces are used to identify error-anchored behavioral slices, add nearby successful examples from the same region, and ask a Teacher LLM to propose a targeted prompt edit. Candidate edits are accepted only when validation performance improves, optionally subject to regression checks. We instantiate the framework with a tree-based slice selector, but the contribution is the contrastive reflection loop rather than the tree itself. On a public HotpotQA retrieval-augmented QA setup, one tree-selected contrastive repair improves held-out exact-match accuracy from 51.4% to 60.4%. Failure-only and random-evidence variants improve less and break more previously correct examples. A light instruction-only comparison places the method near modern prompt optimizers: MIPROv2 reaches 59.4% and GEPA 57.0%. The result is an interpretable optimization loop for IR agents, aimed at making prompt repair more inspectable and validation-driven.
Derek Koh, Jinghui Mo, Benjamin H. Le +7
Prior Prompt Optimization TechniquesContrastive
AskPDF
Sep 8, 2026cs.AI

Closing the Consistency Gap: Self-Evolving Agents That Learn to Stay on Course

Large language model (LLM)-powered agents can be accurate on average yet unreliable in production, a discrepancy that has been observed but remains largely unaddressed. When given the same task five times, a ReAct agent on the AppWorld benchmark using GPT-4.1 succeeds in all five runs only 53% of the time, even though its per-run pass rate averages 77%. We call this 24-point shortfall the consistency gap, and we argue that addressing it is a precondition for trustworthy AI agent deployment. We present a self-evolving agent framework that reduces this gap by identifying unstable, low-consistency steps in agent trajectories and converting them into episodic memory the agent can draw on in future runs. At its core is a Consistency Analyzer that pinpoints where and why a trajectory is likely to flip across executions, and a Guideline Generator that converts the diagnosis into targeted guidelines, committed to memory and injected into future agent executions on similar tasks. On AppWorld with ReAct/GPT-4.1, our framework raises the fraction of tasks that succeed in all five runs by +16 points on same-task evaluation and +13 points on similar-task generalization.
Evelyn Duesterwald, Benjamin Elder, Lilian Ngweta +2
Self-Evolving AgentsAgent FrameworkLearn
AskPDF