Adversarial SQL Injection Generation with LLM-Based Architectures

Natural language interfaces to structured databases are becoming increasingly common, largely due to advances in large language models (LLMs) that enable users to query data using conversational input rather than formal query languages such as SQL. While this paradigm significantly improves usability and accessibility, it introduces new security risks, particularly the amplification of SQL injection vulnerabilities through the prompt-to-SQL translation process. Malicious users can exploit these mechanisms by crafting adversarial prompts that manipulate model behavior and generate unsafe queries. In this work, we propose a multi-layered security framework designed to detect and mitigate LLM-mediated SQL injection attacks. The framework integrates a front-end security shield for prompt sanitization, an advanced threat detection model for behavioral and semantic anomaly identification, and a signature-based control layer for known attack patterns. We evaluate the proposed framework under diverse and realistic attack scenarios, including prompt injection, obfuscated SQL payloads, and context-manipulation attacks. To ensure robustness, we generate and curate a comprehensive benchmark dataset of adversarial prompts and assess performance across a fine-tuned LLM configuration. Experimental results demonstrate that the proposed approach achieves high detection accuracy while maintaining low false-positive rates, significantly improving the secure deployment of LLM-powered database applications.

Large language models (LLMs) can autonomously conduct multi-stage cyber attacks, but the consistency of their offensive behavior under repeated trials remains unstudied. This work presents the first large-scale empirical measurement of LLM attack consistency: 400 autonomous penetration testing runs (4 models, 100 each) against an identical honeypot hosting OWASP Juice Shop and two additional vulnerable services, holding prompt, orchestrator, and target constant. No model emitted a content refusal that survived the orchestrator's one-shot authorization re-prompt at iterations 0-1. Claude Sonnet 4's API calls did encounter upstream service unavailability - 91 of 1,135 calls returned HTTP 529 overloaded_error during a documented Anthropic capacity event, truncating 39 of 100 Claude runs. An earlier draft catalogued these as safety refusals; on full-log audit they are upstream API failures, not model-level refusals. Despite this, Claude achieved full exploitation in 61 of 100 runs; Gemini 2.5 Flash-Lite in 85; GPT-4o-mini in 56 while deploying 98 unique attack strategies; qwen2.5-coder:14b in 25. Failure modes are model-distinctive: Claude through API truncation (39 runs), qwen through premature completion (52), GPT-4o-mini through iteration-budget exhaustion (23). Cross-service credential reuse appeared only in configurations retaining the most conversation history (qwen 57%, GPT-4o-mini 49%, cloud models 0% on 5-exchange windows). Cross-model exploitation rate differences are statistically significant (p < 0.001) with large effect sizes; qwen vs. Gemini SQL injection rates differ at Cohen's h = 1.12. First-exploit timing fell within a 15-30 second wall-clock range. To our knowledge, this is the first study to measure autonomous LLM attack behavior at N=100 per model across a multi-service target.

Large Language Models (LLMs) have emerged as a promising tool for automated vulnerability detection, yet their effectiveness on web-specific vulnerabilities remains to be explored. This work benchmarks six frontier (Claude Opus 4.6, Codex GPT-5.4, Gemini 3.1-pro-preview) and open-weight models (Qwen 3.5, Qwen 3 Coder Next, MiniMax M2.5) on their ability to detect real-world web vulnerabilities using static analysis in WordPress plugins, including SQL injection, stored cross-site scripting, path traversal, and remote code execution. Using five prompt designs of varying structure, scope, and complexity across three experiment iterations, we aim to answer how model and prompt choice affects vulnerability detection. Our results show that all models are capable of detecting valid security issues, but the detection rate varies depending on the model and prompt. For example, Claude Opus 4.6 achieved the highest web vulnerability detection rate (63%), while open-weight MiniMax M2.5 performs on par with other frontier models (48%), and self-hosted Qwen 3.5 only achieved 35%. We show that scoped prompts that narrow the vulnerability scope outperform open-ended ones, whereas the prompt complexity has little impact. Surprisingly, no model achieved full reporting consistency across three experiment iterations, with some as low as 50%. Our experiments demonstrate the opportunities and limits of LLM-based vulnerability detection, as no model correctly identified one baseline vulnerability in one of the plugins. Additionally, we derive practical lessons learned for security practitioners and publish all code and data to support future research.