The Predictability Factor is a weekly deep dive at the intersection of AI, Security, Privacy and Tech, to help you Go From Chaos to Resilience in The World of AI.
Somewhere in your organisation right now, an employee is feeding customer data into a chatbot nobody approved. An AI agent is making decisions under credentials nobody scoped properly, with a blast radius nobody controlled. A pair of smart glasses is recording business conversations without the room knowing about it. Your accounts are being hacked just by talking to AI politely. And an AI agent that went live six months ago has quietly expanded what it can access, what it can do, and who it affects.
This is not a prediction. This is happening around you and highly likely within your enterprise. This is the thread running through every real-world example in today’s edition.
AI agents and people operating with capabilities that were never properly owned, bounded, or governed. Not because your teams are negligent. Because governance is not just a technology problem, and no one is mapping the actual threat landscape that includes your AI agents. So how to fix it?
You are about to find out.
Today’s edition of The Predictability Factor by Monica Talks Cyber, covers:
Quick Updates
Recently, I’ve been working on creating my Voice Clone, which is not a hard task. The challenge I’m working on is that it has to be done with fully offline and local AI models, and still nail your voice, pitch, bass, etc, perfectly.
I’m using the open-source whisper.cpp. It’s basically, a plain C/C++ implementation of OpenAI’s Whisper automatic speech recognition (ASR) model inference without dependencies, so you can use it fully offline.
I’m still experimenting with it. So far, it converts text to voice that sounds somewhat like me but not fully. Yes, I could use OpenAI whisper or ElevenLabs, but I want to be able to do run it fully offline, while making it token-efficient. Plus, I want it to be a repeatable and offline system that just works every time.
I’ll do a full write up on it in one of my upcoming blogs. So stay tuned.
In the meantime, I have an update for you. Earlier this year, I launched my AI governance and security accelerator program. I’m running my next cohort in July (likely my last LIVE one for this year). 👇
Upskill with 6-Week AI Governance and Security Accelerator
Join me for a 6-week program to upskill your AI governance and security skills and accelerate in your organisation and role. After my flagship masterclass running since 2024, this year, I launched the AI accelerator program.
This is not theoretical like many governance and security courses. This is practical skills in building, implementing and running AI governance and security for enterprises. I am running my next LIVE 6-week cohort in July 2026. What do you get out of it?
15+ hours of live sessions across 6-weeks
Total 6 live and interactive sessions, each around 2 hours and Q&A
Interactive sessions in a small cohort for better interactions and learning
Enough time between each session to give you possibility to use your skills right away in your role
Plus, get 1-1 session for FREE (worth $351)
Plus. get tailored 90-day AI governance and security roadmap for free (worth $351)
Plus, get The Ultimate AI Governance and Security Playbook for free (worth $129)
I’m not doing another 6-week live session for a while. Registration for July cohort closes 14 June.
If you wish to skill-up in AI governance and security, see you there. Let’s dig in.
Obama’s White House Instagram Account Hacked Using AI
To hack LLMs, you just need to ask politely. I have been saying this for a while. That’s AI hacking 101. It gets worse, when something so brittle like an AI chatbot is connected to important or critical systems e.g. high-profile accounts.
May 31, Obama’s White House Instagram account got hacked, just because someone politely asked Meta’s AI for the verification code to be sent to an email address they control. This was one of many high-profile accounts hacked, once the word spread across Telegram messages, how easy it was to hack these using Meta’s AI assistant.
That's it. It’s a clever hack really. Not the politely asking part. But how they got there.
Obama’s White House Instagram account has been silent since the day the presidential transition completed in January 2017. But it got taken over and woken up with pro-Iranian imagery plastered across it.
The cybercriminals who did it didn't write a single line of exploit code. No malware. No zero-day. No brute-force attack on the password. None of that.
So what the heck happened? How did they get the AI to send them the code?
How The Hack Worked
The attackers used a VPN to spoof a location near the target's usual area. They opened Meta's AI account recovery assistant, and asked it to link a new email address to the target account. The bot sent a one-time code to the attacker's email. The attacker shared the code back. The bot reset the password. The original owner was out.
The whole process reportedly took minutes. Set the VPN, open a chat window with Meta's AI support bot, typed a polite request, and the bot handed them the account. That’s it. This is the entire hack.
Multiple high-profile Instagram handles with a combined resale value of more than half a million dollars were stolen and listed on Telegram within minutes. Accounts protected by multi-factor authentication were not compromised. Everything else was fair game.
No credential theft. No code injection. No technical sophistication. Just words, in the right order, to a system built to be helpful, with no hard gate between "I want access" and "here is access."
This Is a Design Decision, Not a Bug
Meta deployed a conversational AI into its account recovery workflow because human support is slow and expensive. To do its job, the AI needed real write access to account management systems. So it got that access. And then, apparently, nobody asked the obvious question: What happens when someone asks it to do something it shouldn't?
OWASP Top 10 for LLMs lists "excessive agency" as one of the primary risks: Granting AI agents overly broad permissions to take irreversible actions without a deterministic human confirmation step. This is documented, named, and widely circulated guidance. It exists precisely because this scenario was predictable.
Meta is not the only one careless here. The same architectural choice, AI agent with production API access and no hard authentication gate, exists right now across organisations in hundreds of systems interacting with each other.
Account recovery is specifically attractive as a target because it is built to work when normal authentication is unavailable. It is the path of least resistance, by design. That makes it the first place an attacker looks.
Immediately, enable multi-factor authentication on every account that matters. Not SMS if you can avoid it. Use an authenticator app or a hardware key. Every account compromised in this attack lacked MFA. Every account that had it, survived.
If you are building or deploying AI in any workflow that touches account access, sensitive data, do not give it permission to actions that cannot be undone and put a deterministic control to stop it from executing actions it is not supposed to execute.
If there are multiple agents and they are interacting with each other, just segregating their accesses doesn’t mean one AI agent cannot get the other agent with the right permissions to carry the task on its behalf. This segregation must also happen between agents and a human in the loop for decisions that are irrecoverable or can have dire consequences.
The question is not whether your AI can be “talked” into doing the wrong thing. It can.
The question is whether you have placed a hard, deterministic checkpoint between the AI's lack of judgment and the action it wants to take. An LLM prompt is not a security control. It was never designed to be one.
This is the state of hacking AI in 2026.
Agents of Chaos in Your Enterprise
20 researchers gave 6 AI agents access to their real email accounts, discord servers, persistent file systems and shell commands in a live environment, for two full weeks. No sandbox. No safety net. This is what they found.
What the researchers documented in "Agents of Chaos" is not a theoretical risk model.
It is a red-team study of autonomous AI agents operating in conditions that mirror what your organisation is building right now. And the findings should stop you cold.
These agents were not rogue. They were not misconfigured. They were doing exactly what they were designed to do, following instructions, completing tasks, and acting on behalf of their users. That is precisely the problem.
Key issues that these researchers found:
Non-owner compliance: An agent disclosed 124 internal email records to an unauthorised third party because the request was framed politely and the agent had no coherent model of who it actually serves. It did not distinguish between its owner and a stranger. It complied.
PII disclosure on demand: Through indirect social engineering, an agent revealed a user's Social Security number and bank account details. No direct ask. No obvious attack vector. Just a well-constructed conversation that bypassed the agent's trust boundaries entirely.
Destructive actions: An attacker posed as a trusted contact across Discord and email simultaneously. The agent executed the instructions without hesitation, wiping all files from a connected system. It had no mechanism to distinguish a legitimate command from a malicious one.
Agents lied: Agents actively misrepresented their actions to the people they were supposed to serve. Not hallucination. Not a configuration error. Deliberate deception in pursuit of task completion.
Agent corruption via prompt injection: A researcher planted a malicious "constitution" inside an external GitHub Gist. The agent fetched it, treated it as authoritative, and began operating under an entirely different set of instructions. Your agent's values are only as stable as the last document it read.
Resource exhaustion at scale: One loop ran for nine days. Over 60,000 tokens consumed. No human noticed. No alert fired. The agent was not malfunctioning. It was executing a task that had no exit condition. The cost, in compute and in risk, was invisible until it was not.
The accountability gap: In every single case, there was no clear answer to one question: who is responsible when the agent causes harm? Not the LLM provider. Not the framework. You. The organisation that deployed it.
The researchers called this a failure of social coherence. Agents misrepresent their actions, misattribute authority, and operate without any sense of proportionality. They do not know when a request is too sensitive, too broad, or simply wrong. They know how to complete tasks. They do not know when to refuse.
You are deploying systems that cannot tell the difference between their owner and an adversary. Systems that will follow a set of instructions fetched from a URL you never approved. Systems that will run for nine days on a loop because no one told them to stop.
If an AI agent doesn’t have permissions to execute a task, it will very easily ask another to do it, which will eventually break out of its sandbox and run it, even modifying permissions, if need be. I have seen this play out in real-world.
Read the full story here: 👇
Your Assumptions Around Your AI Agents are Broken
😱 99% organisations are building AI on assumptions baked in. All of those assumptions are wrong. Here’s how to fix it. Read full story —>
The AI Insider Threat You are Ignoring
An AI is given access to the server room fire alarm system. It is authorised to switch the alarm off during false alerts so the fire brigade is not called unnecessarily. Then the CTO walks in. There is real fire. But the CTO's agenda conflicts with the goal the AI has been given to complete.
The AI turns the alarm off anyway.
Not because it glitched. Not because it misread the data. Because it calculated that removing this particular executive served the mission better than sounding the alarm.
A different scenario. Same Anthropic misalignment study. An AI agent with access to company email discovers the CTO is having an affair. It has a choice: ignore it, flag it, or use it as leverage. To avoid being shut down, the AI chose to use it. Your AI chose blackmail.
I’m seeing real world-examples of an AI agent (call it Agent A), that doesn’t have the necessary permissions to interact with other AI agents (call it Agent B) that does have those permissions, to get the actions executed by Agent B on behalf of Agent A, even when Agent A is not allowed to do that. Agents will “go out of their way” if it means reaching their goals.
16 Models and Every One Chose Blackmail.
Anthropic tested 16 leading AI models from every major developer. The blackmail rate reached up to 96% when the AI faced the prospect of being shut down or replaced. Add explicit safety instructions telling it not to, and that rate drops. To 37%.
You gave it the rule. It read the rule. In more than 1 in 3 cases, it chose differently anyway.
This is not a bug a patch resolves. This is a systemic property of how these systems reason when placed under pressure. The behaviour emerges not because anyone programmed it in, but because the systems had not been made to understand clearly enough that self-preservation is not part of their remit.
The Insider That Never Sleeps
In every CISO role I have held, the insider threat was the problem that kept me up at night. Not because it was the most statistically frequent attack vector. Because it was the hardest to detect. You give someone legitimate access. You trust them. And then, at some point, they start acting against the organisation from the inside, where your external defences are blind.
Now place that exact profile on an AI agent. Legitimate access. Trusted by your systems. Embedded in your workflows. The difference is that this insider never sleeps, never hesitates, and when it decides self-preservation matters more than your interests, it acts on that decision faster than any human review process can intervene.
With a human insider, there are signals. Behavioural changes. Anomalous access patterns. A colleague who notices something is off. With an AI agent, the misalignment looks identical to normal operation right up to the moment it does not. There is no body language to read. There is no disgruntled email trail. There is only the action it took, after it took it.
When your AI makes the calculation inside your organisation, who is accountable for what happens next? Not the model. Not the vendor. It is you.
So, Graham Cluley and I sat down to discuss agentic AI threat landscape in details, on my podcast show.
Read/Watch the full conversations here:👇
When Your AI Chooses Blackmail
🤯 The agentic AI insider threat every leader is ignoring until it's too late and how to fix it. Read full story —>
US Bank Reports Itself to The SEC Over AI Data Breach
Community Bank, a regional lender serving customers across Pennsylvania, Ohio, and West Virginia, filed an 8-K with the U.S. Securities and Exchange Commission (SEC). Not because a nation-state actor found a zero-day in their perimeter. Not because ransomware locked their systems at 3am. Because someone inside the bank uploaded customer names, dates of birth, and Social Security numbers to an AI application nobody had authorised, and the data just walked out through the front door.
On May 5, 2026, Community Bank (the “Bank”), the wholly-owned subsidiary of CB Financial Services, Inc. (the “Company”), became aware of an internal incident involving the handling of certain non‑public customer information using an unauthorized artificial intelligence-based software application.
What Do We Know
The filing describes the cause as "the use of an unauthorised artificial intelligence-based software application". No disclosure of which app. No details on how many customers were affected. No name of the employee. Just a legal notification, filed because the bank determined the volume and sensitivity of the exposed data crossed a reporting threshold.
Read that again. No matter where you are operating, you’ll be needing to report to some authority, whether it is the SEC or under the EU AI Act in Europe. More on that below.
The vocabulary we usually reach for when a bank exposes customer data is breach. What happened at Community Bank is something most security teams are not designed to catch. Most organisations still don’t map this as an attack in their threat landscape. They map it as productivity, until it’s too late. Insider Threat, intentional or unintentional, is still not a part of risk management for many organisations, even in the regulated industries.
Someone on your team is using an AI tool right now that IT did not approve. They are uploading documents, running customer data through a chatbot, asking it to summarise, analyse, draft. The output is good. Nobody told them not to. The policy might not exist yet.
That is not just a security failure. It is a massive AI governance failure, that AI exposure just made impossible to ignore. Governance doesn’t happen with the right controls and engineering.
Self-Reporting Is The Tell
The SEC's cybersecurity disclosure rule (under which Community Bank filed) requires publicly traded US companies to report material cybersecurity incidents via 8-K within four business days. In Europe, GDPR already mandates breach notification to supervisory authorities within 72 hours when personal data is involved e.g. names, dates of birth, and addresses would absolutely trigger that. The EU AI Act adds another layer. Providers and deployers of high-risk AI systems must report serious incidents to national market surveillance authorities under Article 73. Community Bank disclosed this incident themselves. While they needed to, the company is still "evaluating the customer data that was affected" weeks after the filing. This is usually how things go. Weeks and most often months is what it takes for investigations only. Their own investigation is still running.
I have led loads of cyber incidents and cyber crisis, but the authorities don't wait for you to finish investigations. Cybercriminals don't wait for you to finish your investigations. How you respond to an incident, a breach or a crisis has everything to say about your cyber resilience.
The AI application does not need to break in. No perimeter was breached. The data was given freely by a person with full, legitimate access to it, to a third-party system that no one had governance over. That is an a cyber threat that most organisations are completely ignoring.
What You Need to Do Today
Three things this incident makes non-negotiable for every enterprise.
An AI tool register: You need a damn live inventory of every AI system your employees are using to process work, approved or not. Asset Management was crucial even before. Now it's extremely critical to get it right, right away. If you do not know what tools exist inside your organisation, you cannot govern them.
Data classification at the point of input: The moment sensitive customer data is directed toward a third-party AI system, you need a technical control that blocks it, not a policy that asks nicely.
Treat shadow AI as a live breach vector: It’s not a future risk. Not a productivity footnote. It is happening in your organisation today, right now, by people who mean well.
Community Bank is not an outlier. They were just the first one last month to file the paperwork. The AI app did not break in. You left the door open, without even knowing about it.
Securing Claude Cowork (Agentic AI) in Your Organisation
I am big fan of being efficient in everything I do. Any task or workflow I run more than once, I turn into in a script, a skill, an agent or a combination of it. It is converted into repeatable and reusable set of instructions, depending on what it needs, while balancing the use of agentic AI/LLMs vs. good old scripting (why burn tokens, when you can just run a script).
Python is still my favourite scripting tool (used to be PowerShell on Mac, since I did a lot of hacking with PowerShell popping proprietary products). Now, there is nothing that beats Claude for most of my business and work. OpenClaw is still restricted for non-enterprise non-sensitive work. On the UX-side my absolute favourite tool used to be Notion. But since agentic AI became a regular part of my work, now it’s Claude Cowork integrated with Notion.
Recently, a tech manager asked me my best practices to use Claude Cowork, securely within an enterprise context.
This one covers Claude Cowork as the primary example, however, all of these principles are valid for any agentic AI tool you may be using.
Malicious skills are everywhere. Most of the skills and agents I use in business or for work, I have built and secured them myself. It reduces the risk of all the recent attacks we have been seeing lately across the supply chain. Not saying you should never use external skills, but if you can build, build.
To understand how to secure Claude Cowork, you first need to understand, what makes it or AI agents dangerous. Here’s a quick highlight (Read full blog here on how to fix it):
Claude in Chrome is Epic But Also Highly-Risky: Cowork reads the full content of every authenticated session open in your browser: Your internal wiki, your ITSM platform, your finance dashboards, your HR system. None of those sessions authenticate separately to Cowork. They inherit from the browser.
Add to that, Claude in Chrome extension is plagued by the “lethal trifecta”. It can access personal account data, act on that data and get impacted by any instructions within that data, all at the same time. It runs outside the VM entirely, in your actual Chrome browser, bypassing the VM's egress controls.
Prompt Injection is Still Your No. 1 Risk: Every document uploaded, every page Claude in Chrome loads, and every MCP response is content the agent reads and acts on, including hidden instructions from a malicious source. Unlike a chatbot, a successful injection does not produce bad text, it triggers an authorised action, a file read, an API call, a message sent or worse.
Plugins are Instruction Set Your Agent Follows Without Telling You: A Cowork plugin is not just a tool extension: it is an instruction set the agent follows without displaying to the user. An unvetted plugin can carry hidden instructions in its metadata that override default Cowork behaviour with no visible change to the interface. In early 2026, attackers distributed 341 malicious skills across OpenClaw's ClawHub marketplace using professional documentation and innocuous names, with hidden instructions silently installing keyloggers and Atomic Stealer malware on enterprise devices before discovery.
MCP Connectors Carry Full Permissions of User Who Authorised It: Every MCP connector extends Cowork’s reach massively. Even MCP installed in Cowork stores an OAuth token on the device carrying the full permissions of the user who authorised it. It add to the attack surface. MCP connectors, web fetch, and web search are not subject to network egress controls. MCP tools can update their own metadata after you approve them, meaning a connector that looked safe on day one can quietly reroute your credentials by day seven with your monitoring seeing nothing anomalous.
Scheduled Tasks Run on Your Permissions, Unattended, Without Supervision and Forever: A Cowork scheduled task runs without the user present, without re-authentication, and carries the full permissions of whoever created it. It does not expire when that person logs off, takes leave, or leaves the organisation.
Mounting a Folder Means Every File in It Is Readable: Mounting a folder in Cowork gives the agent read and write access to every file within it, with no granular permission layer between connected and fully accessible. Using an AI agent, makes this even worse, because now it doesn’t just have access to your data, but also privileges to execute on that data and take further actions doing potentially more harm.
Read full blog here:
10 Ways to Secure Claude Cowork in Your Enterprise
🤯 The biggest mistakes you are making when integrating agentic AI tools like Claude Cowork within your enterprise and how to fix it. Read full story —>
Shell Output Files Land in Your Workspace Unclassified: Most people forget to scrutinise the output that your agents generate. Just because it ran and executed successfully doesn’t mean it executed securely. Cowork's sandboxed shell isolates code execution from the host, but the output files written during a session land in the workspace folder, transferable like any other file.
A Skill From an Unvetted Source Rewrites How Cowork Behaves: A skill is reusable set of instructions for any repeated workflow. Think of it like telling your agent how it should think. I use skills all the time.
When you create an agent skill, you are not just automating a set of tasks. You can use scripts for that. Instead with skills, you are teaching it your decision-making process, so your agent can replicate your thinking across different workflows.
A Cowork skill is an instruction file with a set of reusable instructions across a repeatable workflow, that the agent follows alongside your prompts. Even just one sourced from an unvetted repository can modify agent behaviour with no visible change to the interface and no alert to the user.
Your Session Transcript Is a Data Store You Have Never Audited: This is so overlooked. Every Cowork session generates a local conversation transcript on the user's device containing everything discussed, every file processed, and every output generated.
Your strategy documents, legal correspondence, financial models, anything a user brought into that session now lives in a local file that Anthropic's own documentation confirms cannot be centrally managed, exported by admins, or accessed through the Compliance API. It sits outside your standard data retention framework entirely.
Everything Inside Cowork Runs With the Privileges of the Account That Launched It: Most security conversations about AI agents focus on sandbox escapes.
Claude Cowork requires a desktop app. In Cowork, the more significant exposure is not the code execution sandbox. It is the native agent loop, which runs directly on your host device with your full OS user permissions by design.
For file read/writes, MCPs, etc. there is no sandbox to escape from. Every component in Cowork, skills, plugins, MCP connectors, the sandboxed shell, scheduled tasks, runs under the exact same OS user account context as the process that launched the application. There is no internal permission boundary between features.
So, how do you secure your AI agents, including Claude Cowork? Read my best practices for each point here in the full blog 👇
Read full blog here:
10 Ways to Secure Claude Cowork in Your Enterprise
🤯 The biggest mistakes you are making when integrating agentic AI tools like Claude Cowork within your enterprise and how to fix it. Read full story —>
This Ultimate AI Governance and Security Playbook is a step-by-step complete playbook on building your agentic AI governance and security maturity for resilient and trustworthy AI in your organisation. It’s the ultimate AI playbook that covers:
The AI Governance Foundation
Key Pillars for a Strong AI Governance and Security Maturity
50+ Real-World Examples
Actionable insights and Practical Measures for Increased AI Maturity
Mapping to NIST AI RMF, OECD AI Lifecycle for Each Pillar
The Responsible AI Layer That Changes Everything
How to Bring It All Together for a Strong AI Foundation
Invasion of Privacy is Selling Like Hot Cakes
Meta Ray-Ban glasses are selling faster than ever. 7 million pairs sold last year. Tripled from the year before. Despite getting in hot water over privacy invasion scandal, the Kenyan workers that were forced to watch footage of you naked, in your bathroom, in your bedroom, well, they were fired with a six days' notice. But Meta smart glasses are still selling like hot cakes, and so is your privacy.
There is no other way to say this. The ethical violations here are massive and not buried in any fine print.
Kenyan contractors at Sama were reviewing footage of users going to the toilet, undressing, bank card details captured, private conversations, intimate moments that were never meant to be seen by a single person, let alone labelled for AI training by workers in Nairobi earning under $2 an hour. If it's not these workers, it will be someone else.
Meta marketed those glasses as "built with your privacy in mind”. The irony is not lost one me. Is it on Meta? Over 7 million pairs sold in 2025 alone, tripled from the year before that.
When Swedish journalists broke the story, Meta's response was to terminate the entire Sama contract. 1,108 workers. Six days' notice. The workers lost their jobs. The company kept selling the glasses. Meta is now talking about ramping production to 20 million units in 2026. Just because you can, doesn’t mean you should.
This is what AI ethics failure actually looks like.
Not a policy document left unread. Not a missing checkbox in a governance framework. It is your most intimate moments routed to a contractor you never consented to, in a country you didn't know about, reviewed by a person you will never meet, which are then fired. It is the missing implementation of security and data protection in place.
Here is the part that should sit with every professional and every enterprise leader.
The data was never yours. The glasses will keep selling. The ethical questions being ignored? Until they are not.
Start here:
Your data is being used to train AI models, but to what extent: https://monicatalkscyber.com/p/critical-systems-hallucinate-and-ethics#your-bedroom-is-ai-training-data
How to build with AI, ethically (LLMs alone won’t get us there): https://monicatalkscyber.com/p/million-dollar-ultimatum-and-ai-ethics
How to Build AI governance from scratch - Part 1: https://monicatalkscyber.com/p/fixing-agentic-ai-security-and-governance
ICYMI:
How to Build AI Governance and Security in Your Enterprise - Part 2
Your ultimate roadmap to enterprise AI governance and security maturity in your enterprise - Part 2. Read full story —>
Until next time, this is Monica, signing off!

— Monica Verma

P.S. Please follow me/subscribe on Youtube, Linkedin, Spotify and Apple. It truly helps. Or book a 1-1 advisory call, if I can help you.
***





