When Cisco ran 6,986 multi-turn attacks against 15 flagship models , attackers who adapted across the conversation broke through as often as 88.3% of the time. Amy Chang, Cisco’s head of AI threat intelligence and security research, brought that finding to the agentic security panel at VB Transform 2026 ; the number should worry anyone still running single-turn red-teaming programs. VentureBeat’s June 2026 Pulse survey of 107 enterprise respondents explains why the room was full. More than half, 54%, have already had a confirmed agent security incident (18%) or a near-miss caught before harm (36%). Just 32% give every agent its own scoped, managed identity, and fewer still, 30%, isolate their highest-risk agents in sandboxes. Provider-native and hyperscaler controls remain the primary agent security layer at 82% of companies surveyed . The world’s largest security vendors have done the same math. Palo Alto Networks closed its $25 billion acquisition of CyberArk in February, CrowdStrike agreed in January to pay $740 million for SGNL , and Cisco announced its intent to acquire Astrix Security for a reported $400 million, all of it aimed at the identity and isolation layer most enterprises have not finished building. Chang came to the panel with almost two decades of experience spanning cybersecurity operations, government, and the military. She ran global cybersecurity operations as an executive director at JPMorgan Chase, where she led the bank’s cyber threat intelligence teams, and served as a senior staffer on the House Foreign Affairs Committee and as a U.S. Navy Reserve officer. She also teaches cybersecurity and emerging threats as adjunct faculty at the Middlebury Institute of International Studies. Chang’s 88.3% number comes from a study she co-authored with Nicholas Conley, built on 30,090 single-turn prompts and 6,986 multi-turn attacks against those 15 closed and proprietary flagship models. Multi-turn success rates ranged from 7.89% to 88.3%, every model tested showed non-trivial multi-turn exposure, and the two testing styles did not even rank the models in the same order. Cisco publishes adversarial evaluation signals for what is now 105 models on its LLM Security Leaderboard , she told the audience. “If you don’t understand how models are susceptible to different types of attacks, then you are unable to account for how that model that is powering your agent, that is powering your application, to understand where those failure points are,” Chang said. Single-turn testing is the one-shot malicious prompt, she explained, while extending an attack into a longer conversation “is more realistic of how we are actually engaging with our models, with our agents, with our applications.” That longer arc surfaces harmful outputs and misaligned behaviors that a snapshot never catches. Cisco has pushed the testing itself into agentic territory. Chang described a framework where agents assess a deployment scenario, develop relevant attacks, judge whether they are worth pursuing, execute them, and evaluate their own success. What surprised her most, after all that sophistication, was how simple the defensive answer stays. “The answer is still that it’s pretty simple,” she said. “You don’t have to get super creative. You just need to think about truly what are the fundamentals and basics of what I’m trying to secure in my organization.” Her starting point for CISOs beginning agentic deployments is Cisco’s Integrated AI Security and Safety Framework , which she said “stipulates all the ways that AI can be compromised across the AI lifecycle” from modality through supply chain. From there, teams can work backward from real incidents, trace how each attack was achieved, and use the framework to build a strategy with the right coverage and mitigations. Heather Ceylan, the CISO of Box, sees the same gap from the defender’s side. “A lot of what you see out there with agent red teaming is just single-turn, and that’s not how people are actually interacting with AI day-to-day,” she told the audience. Box now simulates multi-turn adversaries with agents that think like an attacker and iterate attempt after attempt to hijack the target. “You have to pressure test your agents because otherwise you don’t know if your execution controls are really working as you intended.” Box deployed agents inside its security operations center about a year ago, starting with human approval required for every action, and trust built quickly enough that analysts shifted into monitoring mode. Then the agent made one mistake, and every bit of that accumulated trust vanished. “They had to start all over again,” she said. “So I think that that monitoring piece is so important. Even if you’re not gonna have a human in the loop, things change, models change, and we can’t control how the models change and interpret things.” Rajesh Parekh, VP of AI and ML at Intuit, brought the builder’s perspective. Parekh led large-scale computer
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