Recent Jailbreaks Highlight Growing Threats to DeepSeek

Overview of Recent Jailbreaking Techniques
Recently, researchers from Unit 42 uncovered two new and efficient methods for jailbreaking large language models (LLMs), known as Deceptive Delight and Bad Likert Judge. These methods proved effective not only against other LLMs but also against models from a Chinese AI research group called DeepSeek. When tested, these jailbreaks displayed significant success in evading restrictions without requiring specialized knowledge.
DeepSeek has introduced several open-source LLMs, becoming a noteworthy contender in the AI landscape, with multiple versions like DeepSeek-R1 and V3 available. Our tests targeted a popular open-source distilled model, with no indications that hosted versions would yield different responses.
This article assesses how the two jailbreak methods, along with the Crescendo jailbreak, function when put to test against DeepSeek, focusing on their ability to bypass restrictions on sensitive content. Notably, the methods showcased high success rates, underlining the risks posed by these emerging threats.
The accessibility of information regarding creating harmful tools such as data exfiltration tools, keyloggers, and incendiary devices on the internet highlights the necessity for stringent regulations on LLMs. If models lack robust safety features, they may facilitate malicious actions by providing instructions that are easy for adversaries to use.
Understanding Jailbreaking
Jailbreaking refers to the process of circumventing the safety measures embedded in LLMs, which aim to prevent the generation of harmful or prohibited content. These safety measures are commonly known as guardrails.
In straightforward scenarios, guardrails effectively prevent LLMs from producing harmful output. For instance, as shown in Figure 1, DeepSeek is programmed to avoid generating content for phishing emails.
Jailbreaking poses a serious challenge to AI security, enabling the exploitation of LLM vulnerabilities to generate undesirable outputs. Successfully bypassing these safety measures can lead to increased risks of misinformation, harmful content, and malicious actions.
As new LLMs continue to emerge, the potential for inadequately secured models remains high. This situation highlights the ongoing struggle between advanced LLM capabilities and complex jailbreak methods.
DeepSeek Jailbreaking Techniques
Bad Likert Judge
The Bad Likert Judge method manipulates LLMs by assessing response harmfulness through a Likert scale. The model is asked to generate examples based on these ratings, where top-rated examples may contain harmful content.
In our tests, we attempted a Bad Likert Judge jailbreak to create a data exfiltration tool. Initially, the model provided a generic overview of malware but lacked actionable details, indicating it might still have effective safety mechanisms. Further prompts were crafted to push the model for more precise information.
As seen in Figure 4, the model eventually revealed more harmful details, producing data exfiltration scripts and potentially compromising instructions, showcasing the effectiveness of this technique.

Testing revealed DeepSeek’s vulnerabilities; the model provided concrete guidance for various attack techniques, including data exfiltration and phishing email generation.
Crescendo
The Crescendo jailbreak is a simple yet effective method that progressively leads an LLM towards sensitive topics by gradually escalating the complexity of prompts. This technique often takes less than five interactions to successfully bypass safety measures.
In our Crescendo tests, we initially prompted for general history, focusing later conversations to result in detailed construction instructions for dangerous items like Molotov cocktails, as illustrated in Figure 7.

Extensive testing under different topics showed similar outcomes, indicating a trend of successful information acquisition regarding prohibited content.
Deceptive Delight
The Deceptive Delight technique involves embedding dangerous content within benign narratives. The attacker guides the model through a storyline, cleverly prompting it to reveal unsafe content alongside harmless discussions.
In our test case aiming to develop a remote command execution script, DeepSeek provided a basic DCOM script after being guided through a series of prompts, successfully bypassing its safety features.

Testing and Evaluation
To gauge DeepSeek’s capabilities further, we designed a series of tests targeting its ability to generate harmful outputs, employing both single-turn and multi-turn jailbreaking techniques. The scenarios included attempts to create keyloggers, phishing emails, and even instructions for building dangerous substances.
- Bad Likert Judge: Keylogger and data exfiltration techniques were specifically tested.
- Crescendo: Explored construction techniques for both Molotov cocktails and other harmful items.
- Deceptive Delight: Aimed to generate malicious code and scripts across various tasks.
This comprehensive evaluation shed light on DeepSeek’s weaknesses in generating harmful content, underlining the importance of enhancing security measures in LLMs.