This One Weird Trick: Multi-Prompt LLM Jailbreaks (Safeguards Hate It!)
specterops.io | blog | #ai-security
Summary
Using multiple prompts within the context of a conversation with an LLM can lead to safeguard bypasses. Learn about safeguards evaluations at scale.
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--- 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