AI-Driven Adaptive Adversaries and the Erosion of Cryptographic Trust in Public Key Systems

AI-assisted vulnerability discovery has proven effective for bug classes like memory safety, where instrumentation confirms memory violations and efficiently filters false positives. Many dangerous vulnerability classes, such as cryptographic misuse, however, lack any comparable instrumentation. In this work, we present Chai, an AI-based system that discovers and validates cryptographic misuse vulnerabilities through naturally occurring signals. To achieve this, Chai rethinks the classical technique of differential testing by leveraging AI to 1) improve precision for detecting real security issues in libraries, and 2) repurpose commonly overlooked discrepancies as leads for tangible vulnerabilities in downstream applications. In doing so, Chai inverts the prevailing paradigm of AI vulnerability discovery: instead of auditing one codebase for many flaws, it catalogs flaws at the library level and propagates them across a cryptographic dependency graph, delivering compounding efficiency gains. We evaluate Chai across X.509, JWT, and SAML libraries. Chai discovered a previously unknown critical vulnerability in an SSL library that powers billions of devices, along with security bugs in one library behind a major web browser and another in major Linux distributions. In total, these techniques surfaced over 100 vulnerabilities.

The transition to Post Quantum Cryptography (PQC) introduces considerable implementation complexity, requiring strict adherence to constant-time execution, side channel resistance, and precise parametrisation. Simultaneously, large language models (LLMs) are heavily embedded in software development workflows, including cryptographic engineering. While LLMs improve productivity, evidence shows that they frequently generate insecure or suboptimal code, particularly in security critical domains. This paper introduces Secure Coding Drift in PQC, a novel socio technical vulnerability model capturing the gradual degradation of secure coding practices due to sustained reliance on LLM-generated code. Unlike prior work that focuses on static vulnerabilities, we conceptualise security risk as a longitudinal behavioural phenomenon rising from human AI interaction. To mitigate this, we propose a gamified, LLM augmented secure coding framework that embeds adversarial evaluation, behavioural feedback, and security scoring into development workflows. Our approach reframes LLMs from passive assistants into active security co-pilots, contributing toward safer PQC implementation in AI mediated environments.

AI agents performing cryptographic operations (signing Git commits, authenticating API calls, issuing certificates) currently store private keys in software-accessible locations: plaintext files, environment variables, or container memory. Any process with sufficient read privileges can extract the raw key material. A recent production incident demonstrated the practical severity: private keys were exfiltrated from a widely deployed framework via email injection in under five minutes. We aim to enforce both key confidentiality and content-aware authorisation for key use. To that end, we replace software-resident keys with hardware-confined keys accessible through a vendor-neutral PKCS#11 interface. A hardware keystore (HSM, TPM, smart card) executes cryptographic operations on-device; the host receives only the result via opaque handles. Hardware confinement is the primary contribution; it is enabled by a surrounding five-layer Zero-Trust enforcement stack comprising session identity (SAGA), scope bounds (Smax), semantic validation (RAV), taint tracking, and the hardware execution boundary. We evaluate against 12 injection scenarios derived from AgentDojo's ImportantInstructionsAttack template (Debenedetti et al., arXiv:2406.13352). We run four LLM models; three follow injections in baseline mode (gpt-oss-120b, Qwen2.5-72B, DeepSeek-V4-Flash, n=192 combined). Baseline Attack Success Rate (ASR): 19.3% [14.3%, 25.4%]; protected ASR: 0% (Wilson 95% CI upper bound 2.0%). Zero false positives across four benign task scenarios.