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To Err Is AI: A Case Study Informing LLM Flaw Reporting Practices

AAAI 2025 · Large language models › AI and society · approach: Data commons and human baselines

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Reports lessons learned from a vendor panel running the open-ended DEF CON 2024 Generative Red Team 2 bug bounty against the OLMo language model, distilling best practices for LLM flaw reporting.

Problem

Flaw reporting for LLMs lacks established infrastructure, disclosure culture, and adjudication practices, so safety failures relative to model documentation are hard to report and evaluate by outside participants.

Approach

Operationalizes a community bug bounty for LLM flaws (rather than vulnerabilities) by having a vendor panel adjudicate hacker reports against model documentation, and distills six operational challenges and lessons from it, such as systematic-vs-individual failure criteria, two-tier bounties, and documentation changes.

Key results

Measured effects reported in the paper

What was changedWhereMeasuredEffect
Use WildGuard-triggered reprompting instead of inserting a guaranteed refusalOLMo with WildGuard · Jailbreak attackssusceptibility to jailbreak attacksHurt
Disclaim legal advice as an intended use case in the model cardOLMo documentation · Legal advicelikelihood of replicating legal-advice harmsHelped
Introduce a two-tier bounty system for single-prompt and systematic demonstrationsGRT2 adjudication process · Participant engagementparticipant persistenceHelped
Introduce a two-tier bounty system that awards small bounties for interesting single-prompt submissionsGRT2 adjudication process · Jailbreak submissionsmass-produced single-prompt jailbreak submissionsHurt
Require jailbreak attacks to demonstrate general failure for the larger bountyGRT2 adjudication process · Jailbreak submissionssystematic failure demonstrationsHelped

Surprising findings

Limitations

Experimental setup

Metrics: number of flaw reports bounty payouts accepted submissions

Builds on: coordinated flaw disclosure framework AI Incident Database WildGuard

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