---
id: 9495
title: "This One Weird Trick: Multi-Prompt LLM Jailbreaks (Safeguards Hate It!)"
source_domain: specterops.io
source_url: "https://specterops.io/blog/2025/09/05/this-one-weird-trick-multi-prompt-llm-jailbreaks-safeguards-hate-it/"
published_at: "2025-09-05T16:12:20Z"
tags: ["ai-security"]
phying_url: "https://phying.com/item/9495"
lang: en
---

# This One Weird Trick: Multi-Prompt LLM Jailbreaks (Safeguards Hate It!)

## Summary

Using multiple prompts within the context of a conversation with an LLM can lead to safeguard bypasses. Learn about safeguards evaluations at scale.

## Intelligence Metadata

- **Sources:** specterops.io
- **Published:** 2025-09-05T16:12:20Z
- **Original:** https://specterops.io/blog/2025/09/05/this-one-weird-trick-multi-prompt-llm-jailbreaks-safeguards-hate-it/
- **Phying News:** https://phying.com/item/9495