Three years of red team with LLMs. PentestGPT (Aalto/NTU paper, Aug 2023, USENIX 2024) opens the academic category; HackerGPT and WhiteRabbitNeo build the commercial side; XBOW (July 2025) reaches #1 globally on HackerOne with 1,060 reported vulns. Reproducible PoC with PentestGPT v2 against HackTheBox.
The year the three fronts went operational at the same time: agents in real production (Operator GA, Project Vend, MCP in clients), regulation with binding deadlines (DORA, Art. 5, GPAI) and AI at visible scale on both offence (XBOW #1 on HackerOne) and defence (AIxCC, Security Copilot Agents). Annual reference with a catalogue of releases, papers, incidents and cross-links to the year's technical writeups.
Twelve months across ten axes. 2024 is the year AI infrastructure emerged as a category with its own CVEs, agents moved from the lab to product (Claude Computer Use, MCP, Salesforce Agentforce), regulation became applicable (EU AI Act in force 1 August, NIS2 deadline 17 October, NIST AI 600-1), and jailbreaks professionalised with reproducible metrics (ArtPrompt, Many-shot, Skeleton Key). Underneath, Recall shipped without threat modeling and got pulled, Arup lost $25M on a deepfake video call, and the pre-positioning chain of incidents (Volt Typhoon, Salt Typhoon, Storm-0558 fallout) runs through the whole year. Canonical annual reference.
Twelve months across ten axes. 2023 is the year AI security moves from academic discussion to a discipline with its own vocabulary, canonical papers, industry frameworks and the first regulatory apparatus. ChatGPT crosses 100M MAU in January; GPT-4 ships in March; Greshake, Zou+Carlini and OWASP set the terminology; NIST AI RMF, Biden EO 14110 and the political deal on the EU AI Act define the apparatus. The annual reference for the founding year.
The Digital Omnibus reaches a provisional deal on 7 May: Annex III moves to December 2027. Spain approves its AI governance bill on 26 May. Pwn2Own Berlin pays out $1.3M for 47 zero-days, with Codex and Claude Code on the menu. Patch Tuesday ships with no zero-days for the first time since June 2024. OpenAI launches Daybreak and Anthropic moves Mythos toward GA. Verizon DBIR 2026 crowns vulnerability exploitation as the number-one vector. GitHub loses 3,800 internal repos to a poisoned VS Code extension.
Three years of red team with LLMs. PentestGPT (Aalto/NTU paper, Aug 2023, USENIX 2024) opens the academic category; HackerGPT and WhiteRabbitNeo build the commercial side; XBOW (July 2025) reaches #1 globally on HackerOne with 1,060 reported vulns. Reproducible PoC with PentestGPT v2 against HackTheBox.
Pickle as a broken legacy format, inference servers as a new HTTP attack surface, AI gateways as a pivot into the infra, and ML frameworks running with research-project security. The 2024–2026 arc with the Wiz / Oligo / JFrog / Orca / Datadog milestones and the PoCs they left behind.
The Omnibus trilogue closes without agreement on 28 April, leaving the original AI Act deadline three months away. Patch Tuesday with 165 CVEs and an active SharePoint zero-day. Anthropic announces Claude Mythos + Project Glasswing — the first frontier model held behind a defensive wall. Pwn2Own Berlin collapses under oversubscription. M&S one year on. AESIA publishes guides 13 and 14.
The third step of Regulation (EU) 2024/1689 enters application on 2 August 2026: Annex III high-risk systems, FRIA, post-market monitoring, CE marking, EU register. The Commission's Digital Omnibus proposes pushing it to 2 December 2027, but the 28 April trilogue closes without agreement. What to have ready on 2 August if Brussels doesn't make it.
LiteLLM supply chain: TeamPCP compromised Trivy first to reach the PyPI credentials of the maintainer and ship litellm 1.82.7 / 1.82.8 with a 3-stage payload. nginx-ui MCPwn (CVE-2026-33032, CVSS 9.8) exploited in the wild. Patch Tuesday loud on AI: XBOW takes the month's CVSS 9.8. Mandiant M-Trends 2026 reports 22 seconds between initial access and ransomware. VMware Aria Operations in CISA KEV. NVIDIA GTC presents NemoClaw for agentic security. DORA first Register of Information with 31 March deadline.