Testing the Oracle: Challenging Chat GPT's Security Filters to Counter Terrorist Use

Rumyana van Ark, Tarik Gherbaoui, and James Patrick Sexton (eds.), Countering Terrorism and Violent Extremism in the Public Interest (T.M.C. Asser Press/Springer) 31 Pages Posted: 31 Jan 2026 Università degli Studi della Tuscia Date Written: June 17, 2025 This Chapter explores the criminal risks of Chat GPT, a large language model (LLM) developed by OpenAI. While Artificial Intelligence (AI) technologies like Chat GPT enhance daily life by simplifying complex tasks and fostering creative endeavours, they also pose substantial risks when exploited for illicit purposes. This Chapter primarily investigates how Chat GPT's built-in ethical restrictions and filters, designed to prevent the dissemination of harmful content, can be circumvented-a practice known as "jailbreaking"-for terrorist use. Chat GPT, despite its advanced capabilities, does not truly comprehend context or intent but rather operates on probabilistic pattern recognition. Therefore, this limitation can be exploited to extract sensitive information or facilitate activities contrary to the model's ethical programming. Through various experiments, it will be demonstrated that while OpenAI's safeguards are generally effective, creative rephrasing of prompts can sometimes bypass these protective measures, revealing potential vulnerabilities in the model's response mechanisms. Hence, examining how terrorists could potentially leverage AI tools like Chat GPT for propaganda and recruitment, a broader discussion on AI regulation and the ethical deployment of these technologies might be needed. The findings call for a nuanced approach to AI governance that balances innovation with stringent safeguards to mitigate risks, particularly in the realms of cyberterrorism and online radicalisation. Keywords: Artificial Intelligence, AI Law, Chat GPT, Counter-terrorism, Cyberterrorism, Jailbreaking, Propaganda, Social Media Suggested Citation: Suggested Citation Rumyana van Ark, Tarik Gherbaoui, and James Patrick Sexton (eds.), Countering Terrorism and Violent Extremism in the Public Interest (T.M.C. Asser Press/Springer) Rettorato, Via S.M.in Gradi n.4 Viterbo, 01100 Italy Securities Law eJournal Subscribe to this fee journal for more curated articles on this topic