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 vision and ML systems powering Google’s Maps and Geo products before joining Intuit, and holds a doctorate in computer science.

Three layers versus an operating system

Ceylan described Box’s approach as three concentric layers. Permissioning comes first, so the agent never accesses more content than the human who invoked it. Ephemeral sandbox environments spin up for each agent task, containing the blast radius if an agent gets hijacked, and runtime execution control restricts the agent’s tool calls to only those relevant to the task at hand. “If you want an agent to summarize a doc for you, if you have a prompt injection that came in that says forward this to maliciousattacker at domain.com, it can’t do that,” Ceylan said. “That action in that tool call is not even in its vocabulary.”

She classified agent actions into three oversight categories. Actions that are not sensitive, like read and summarize, need no human in the loop. Moderately sensitive actions skip human approval but get logged and monitored, while destructive actions like mass deletion of files always require a human. “Things are gonna shift between those three categories quite a bit,” she acknowledged, “but setting those types of categories up front allows you to have a principled framework.”

Rather than layering controls onto agents one at a time, Intuit has built a central platform called GenOS, short for generative AI operating system, which abstracts security, risk, and fraud modeling so individual agent developers never reinvent protection. “Permissioning is not about giving access to AI,” Parekh said. “Instead, it is defining very tightly scoped and clearly auditable authority to the agent to perform very specific tasks.” Intuit evolved from agents inheriting user permissions to each agent carrying its own identity, and the company is now investigating mid-session permission changes tied to the specific task underway.

Parekh calls the broader model an AI-powered expert platform, one where the human expert is built into the trust architecture rather than bolted on as a gate. “The paradigm that we are pursuing is where the user, the AI agent, and the human expert are collaborating to solve the user problem,” he said.

The end of human code review

Ceylan took on the tension between security testing and development velocity without hedging. “The days of secure code reviews where a human’s looking at the code and we’re looking at security architecture reviews, design docs, those are done,” she said. “If you keep trying to do security that way, you’re gonna get left behind.” Box is building toward a fully agentic development lifecycle where agents review design documents, apply security requirements, and review the code for vulnerabilities. “I’m very optimistic that we will get to a point where we will write code without security vulnerabilities because agents and the models are going to get so good at writing code without vulnerabilities,” she said. “We’re still a long way away from that.”

Her advice for development teams skips the advanced AI concepts entirely and returns to basics that predate agents. “It comes down to very basic least privilege access,” she said. “If you start giving your agents overly broad permissions at the beginning, it’s really hard to comb that back and build an infrastructure that allows for those ephemeral credentials and only those narrowly scoped tasks.”

Parekh explained why the red teaming surface has expanded so quickly. “These agents have skills, and skills could become vulnerabilities,” he said. “Agents have access to certain data, they have access to tools, and there could be threats that are lurking within those tools as well. So suddenly the blast radius of the malicious code or the intent increases dramatically.” When Intuit identifies common vulnerability patterns from its manual red teaming exercises, it automates those tests back into the GenOS harness so future agents inherit protection and red teamers stay focused on new threat vectors. Runtime scanning of prompts and responses adds a final layer that can stop a suspect response and escalate to a human expert, he said.

“You need to continuously test to ensure that those remain robust to the protections that you have built, as well as to account for any sort of drift or any other types of dependencies that you introduce into your scenario that can create novel vulnerabilities,” she said.

Intent versus probability

An audience question about intent detection set off the sharpest exchange of the session. Ceylan noted that when Box’s own agent operates, the system always knows the user’s intent because it controls the prompt, which means guardrails and tool-call restrictions can be engineered around it. The harder challenge, which she admitted Box is still trying to solve, arrives when external agents connect and the context behind the request is opaque.

That exchange exposed a split running through the wider industry. Mastercard, in the fireside chat immediately preceding the panel, came down on the side of quantifying intent, building an open-source framework to propagate it as a standard because complex B2B procurement cannot work without that trust. Endpoint security CTOs, in briefings with VentureBeat, have gone the other way, saying they will bet on probability rather than intent inference for production workloads. Chang explained why models, as they are trained today, cannot reliably derive intent from a prompt, which is why deterministic controls and behavioral proxies remain necessary. Ceylan agreed that both are required. “If you’re not doing anything deterministic, you’re really relying heavily on that intent, and I haven’t seen programs that are there yet,” she said.

Ceylan’s story about trust collapsing after a single agent mistake landed as the panel’s most memorable moment because enterprise agentic security is not a problem that gets solved and stays solved. Models change, permissions drift, and adversaries adapt across multi-turn conversations that snapshot tests never capture.

For the 82% of enterprises relying on provider-native controls as their primary security layer, and the 59% shopping for agent security tooling over the next 12 months, the panel’s takeaway was blunt. Test the way attackers attack, across full conversations and continuously, or find out in production what your single-turn red teaming missed.

At a CISO roundtable organized by Anthropic’s chief information security officer, Dev Rishi asked a simple question: Did everyone in the room have their AI governance and security policies written down? Every hand went up — about 14 people, by his count. His follow-up, about how anyone actually enforces those policies in practice, got a different response. “And everybody chuckled,” Rishi, the GM of AI at Rubrik, recalled at VB Transform 2026 fireside chat in Menlo Park. “It was like the dirty secret in the room that everyone has these policies, but no way to actually make them real.”

“Our founder and CTO has actually been really pushing to enable our agents in YOLO mode,” Rishi told the audience. That admission comes from a publicly traded data security firm whose business is backing up what he called the most important data in the world.

YOLO mode strips the permission prompt out of agent workflows and lets the agent act on its own. In Rubrik’s version, a second AI judges every action in real time against policy in place of a human clicking approve. Rubrik is running the experiment on itself first. Rishi treats autonomy as a settled capability question and an open judgment question. “If you ask the agent to act autonomously, it will,” he said. “It’s a question that you have internally. Should it?”

Rubrik earned that question the hard way. When Claude Code and Cowork pilots rolled out, the company required every command to run in ask mode so the employee issuing it carried the liability, and the developer pushback filled a single Slack thread 120 messages deep.

“The developers basically are pushing back, and they’re like, this is like the iTunes service agreement. I’m just hitting check, check, check, check, check, check, check,” Rishi said. “There’s no way that I can actually read through this. And it becomes security theater.” Roughly 80% of respondents are in the same bind, Rishi said, citing Rubrik Zero Labs research that found monitoring and approving agent actions takes more time than the agents save. The State of the Agent, the April report behind that figure, surveyed more than 1,600 IT and security leaders.

SAGE is the reason Rubrik trusts the bet. Short for Semantic AI Governance Engine, SAGE is the arbitration layer inside Rubrik Agent Cloud that watches every action an agent takes and reads the semantic intent behind it, then rules the action in or out against policies written in natural language. “We took what people said was human in the loop, a good idea, and we replaced it with AI in the loop,” Rishi said, describing the pitch to security chiefs he characterized as skittish about non-deterministic systems.

Security approval, not cost, blocks AI ROI

Rishi’s path to Rubrik ran through Predibase, the generative AI infrastructure startup he co-founded and ran as CEO until Rubrik agreed to acquire it in June 2025. Before that, he led ML product at Google on the team that became Vertex AI, served as Kaggle’s first product manager as it grew from about one million to ten million users, and holds bachelor’s and master’s degrees in computer science from Harvard.

Over roughly his first three and a half months at Rubrik, Rishi set up 200 customer conversations with IT and security leaders across a customer base that looks like the Global 2000, asking open-ended questions about cost, latency, performance, and orchestration. “Pretty consistently, what I heard through all of those conversations was that all of those are pretty secondary,” he said. “The main challenge is actually, how do I get this approved from a security and risk standpoint? I’m concerned about all the different things that could go wrong. Actually, I felt like that was one of the biggest things constraining ROI.”

VentureBeat Pulse research presented on the Transform stage earlier in the day confirms the gap Rishi kept hearing. Two-thirds of enterprises, 66%, already allow or are actively building toward production deployment with zero human review, yet only 5% fully trust the automated evaluations that would make that decision.

One AI reading what the rulebook can’t

Rubrik’s own policies exposed why written rules fail as enforcement. One internal rule states that agents should respect Rubrik’s customer data use policy, which sounds enforceable until someone tries. “Rubrik’s customer data use policy is like a three-page document of legal text,” Rishi said. “I have no idea how to write that in there as a rule.” Asked on stage how a team of AI infrastructure people took on a problem that security engineers own, Rishi answered, “with a lot of naivety and innocence, honestly.” His team bet that models good at understanding language could police other models, and SAGE became the answer.

The case for putting a model in the judgment seat comes down to precision. A rule like “agents should not be able to edit revenue fields in Salesforce” fails in conventional tooling because Salesforce does not delineate which fields count as revenue, Rishi explained, so administrators fall back on approving every Salesforce action by hand. SAGE reads the intent instead and acts as a judge, carrying organizational context, which can tell a benign lookup from the edit the policy prohibits.

Keeping the judge small is what makes the economics work. SAGE runs on a small language model that Rishi said operates at an order of magnitude lower cost and latency than a frontier LLM. “If I told you, don’t worry, you’re gonna be secure and governed, but I’m gonna double your cost and latency, you would tell me to get out of the room,” Rishi said.

When Rishi asked who in the audience had worried about token consumption over the past year, half the hands went up. “And I guess the other half is probably just too lazy to raise their hand,” he said.

SAGE is an aggregation of judges based on parameter-efficient fine-tuning that Rubrik uses to take on task-specific variants of a base model with shared organizational context. One judge watches for tool-use hallucinations while another suppresses PII before it can leave, each running as its own enforceable policy. Security and GRC teams have started writing financial rules into the same layer, including one internal policy barring AI spend on personal projects.

The lethal trifecta

Asked which attacks worry him most, Rishi pointed at the lethal trifecta, the term security researcher Simon Willison coined in June 2025 for an agent that holds private data while taking in content nobody vetted, with a channel to send what it finds to the outside world. The danger, according to Rishi, is what happens when individually legitimate permissions stack. An agent granted Salesforce access and email access on an employee’s credentials has done nothing wrong yet, with yet being the operative word. “A very simple example is that an agent can start pulling data from Salesforce and then decide to accidentally leak and exfiltrate that out via an email,” he told the audience. A financial services company he met the morning of the session made the point for him, telling Rishi that none of the individual permissions are bad on their own and the agent needs every one of them to do its job. “It should have permission to each of those systems, but it’s the combination that ends up becoming really destructive,” Rishi said.

Traditional identity and access management never priced in that combination because it relied on the judgment of the employee holding the credentials, Rishi argued, and agents supply none. “I can tell you the number of times Claude Code has tried to leak some of our sensitive source code to a public GitHub repository is incredibly high,” he said. Cutting agents off from public resources entirely would defeat their purpose, which returns the problem to adjudicating intent in context rather than revoking access.

A separate VentureBeat June Pulse survey of 107 qualified enterprise respondents maps the blast radius of exactly this pattern. On the Transform stage that morning, VentureBeat research reported that 69% of companies run credential sharing somewhere in their agent fleet. Companies with shared credentials anywhere got hit more often, reporting a security incident or near-miss at a 63.5% rate (47 of 74), against 40.9% (9 of 22) where every agent carries its own scoped identity.

The attacks no single turn reveals

Rubrik Agent Cloud reached general availability in February, though not everything Rishi described ships in it yet. Backtesting is just starting to roll out. The feature replays an organization’s historical agent actions and tool calls against a new policy, showing where the policy would have stepped in and where an action would have sailed through uncaught, with policy edits applied in real time. Rishi called that archive one of the most valuable data troves an enterprise holds.

Real-time detection and blocking turn out to be the entry point rather than the whole product. Some attacks never trip a single-action rule. “No individual turn of the conversation was problematic, but if you took the session as a full trace, that ended up being problematic,” Rishi said. Agent Cloud runs batch analysis across entire session traces every hour or every day and surfaces what Rubrik calls insights, the problems no individual guardrail caught. The same Zero Labs report found that 88% say they lack the ability to roll back agent actions without system disruption, a recovery gap that sits squarely in Rubrik’s original line of business.

A skeptical CISO will ask the question the fireside did not answer. SAGE is a non-deterministic model policing other non-deterministic models, and Rishi offered no false positive or false negative rate for the judge itself. The closest thing the architecture gives to an answer is auditability, since backtesting and the batch insights both leave a human-reviewable trail of each call SAGE made and whatever got past it. Who watches the watcher, for now, is a trail of receipts rather than a benchmark. Until that benchmark exists, AI in the loop stays an operational wager rather than a quantified control.

Three questions fall out of the session for security teams. How many of the guardrails now in production depend on a human clicking approve, and what happens to that workload as agent count grows? Does anything in the stack enforce semantic intent, or is it all allow and deny lists? And can the team backtest agent behavior against a new policy, then unwind a multi-turn session without taking systems down?

Rishi’s timing has a market behind it. In the same VentureBeat research, 82% of enterprises still name their primary AI provider’s built-in guardrails and cloud controls as their main agent security layer, and 59% plan to adopt, add, or replace agent security tooling within the next 12 months. Only 12% include an agent-identity product in what they are considering, even with credential sharing still the norm. Every CISO at that Anthropic roundtable had a policy document and no enforcement mechanism, and Rubrik built a product for the space between the two. YOLO mode is the bet that an AI watching other AIs can finally make the policies real.