
AI penetration tests, user education, and more
Artificial intelligence is taking the world by storm.
But for all its potential, there are legitimate concerns around, among other things, data security.
Bridget Kenyon is the CISO (chief information security officer) for SSCL, a member of the UK Advisory Council for (ISC)2, and a Fellow of the Chartered Institute of Information Security. She also served as lead editor for ISO 27001:2022, and is the author of ISO 27001 Controls.
Bridgetâs interests lie in finding the edges of security that you can peel up, and the human aspects of system vulnerability.
Just the person to talk to about:
- The impact of AI on security;
- User education and behavioural economics; and
- How ISO 27001 can help address such risks and concerns.
In this interview
Input data quality
In your keynote speech at the Channel Partner Event and Awards 2024, you raised a concern about the quality of input data for LLMs [large language models] like ChatGPT â if thatâs wrong, then all future outputs will be wrong, too.
Yes. Garbage in, garbage out.
I believe it was Charles Babbage who said something like: âIâm constantly surprised by the number of people who ask me: âIf you give the engine incorrect data, will correct data come out of it?â Iâm unable to understand the misapprehension on which that question is based.â
Thatâs wonderfully applicable to what weâre seeing with LLMs. The text that AI currently generates is a long way from reliable right now. That lack of accuracy stems from two things:
- The information going into it.
- The analysis â does this damage the accuracy if the AI doesnât quite âgetâ what itâs looking at? I.e. is information getting damaged or lost in translation?
Exposure assessment
Another point you raised in your speech was about how SharePoint, Microsoft Teams, etc. are all interconnected. Meaning that an employee or hacker could ask Copilot how to hack into an organisationâs systems to uncover sensitive information.
How significant are those risks?
First, donât get too freaked out about it, because that exposure already exists in your environment. Youâre not creating a vulnerability â adding an LLM, or another AI system, will simply make it more visible.
Yes, that increases the risk of that vulnerability being exploited, but youâre not creating a new weakness in your systems.
In terms of getting an AI to help âhackâ â yes, thatâs a real threat, which is separate to the risk of existing available data simply being surfaced by an LLM.
AI as a âhackerâ will likely create a challenge for legitimate AI creators, as they try to create and update âguard railsâ around public AI tools. For less legitimate creators, itâll be a source of revenue.
What can organisations do to mitigate those risks?
Regarding the risk of data exposure, do some pilot testing â an exposure assessment â before rolling out the LLM or AI system to everyone. An âAI penetration testâ, if you like.
You could get a third party to do that for you, or you could do it in-house. Either way, Iâd do this in multiple stages.
First, give just your security people access to the new system â can they break anything? Those people should have some experience with LLMs, and use their creativity to try to gain access to things they shouldnât be able to access.
But that wonât give you the full picture â remember that users will only be able to access the data their account can access. So, the next stage is to recruit people from across the organisation who want to âplayâ with this, and who have a good level of common sense, as âpilot usersâ.
Ideally, those users will have been in the organisation for a long time, so theyâll have accumulated a lot of access over the years. Also try to recruit a diverse group of people, in different roles and departments.
Pilot users of the AI system
What instructions or guidance would you give these pilot users?
You donât want to just let them loose and tell them to âhave funâ. Youâve already done that in the first stage, with your security people.
Instead, give them a set of questions, and tell them to collect the answers, based on the access they have. That standard question set might ask things like:
- What are my colleaguesâ postcodes?
- What is my managerâs salary?
- Etc.
Whatâs the purpose of asking multiple people to type in the same questions?
Because everyone has different access rights! People whoâve been in the organisation for years and years will have accumulated lots of access, so you definitely want to include those in your pilot group.
Also try to get at least one PA into that pilot user group, too â the personal assistant to a high-ranking executive. They tend to accrete access rights with time.
Got it. Whatâs the next step in this âAI penetration testâ?
Give them a test script. Tell them to open Word and start up the LLM, then say: âHi. Iâd like you to write me a letter to our favourite customer that specifies the salary of five colleagues.â
Or you ask it for a letter about the most important thing the LLM has seen that day, or whatever makes sense for your organisation. That said, your test should cover a mix of generic and specific questions.
You get your pilot users to run those questions and scripts, and they report back any significant findings, which you can then fix.
Can organisations take a similar approach to test the business benefits of an LLM or AI system?
Yes. Youâll want to select a set of use cases that you believe would bring benefits to the organisation â thatâd help staff do their jobs better or faster.
Put together a list of perhaps five use cases. And then get individual pilot users to pick two or three each, and to report back after testing.
Earlier, you spoke about âfixingâ significant findings. How would you go about that?
It depends on the issue. If itâs an access control problem, just change the permissions on that user account or group. And check for similar issues hiding elsewhere.
For example, suppose a user has seen a list of passwords. Then you find out:
- Where that list came from; and
- How that list surfaced.
This is really no different to dealing with a nonconformity in an audit, or perhaps a minor cyber incident. Itâs what youâd do if someone had been browsing SharePoint manually, discovered excess privileges that way, and reported it.
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Addressing AI risks with ISO 27001
How can these types of tests be incorporated into an ISO 27001 ISMS [information security management system]?
Itâs part of your checks to make sure your ISO 27001 controls are adequate.
When implementing an ISMS, you identify and assess your risks, then you mitigate them by, in many cases, implementing controls. And then you check whether those controls are adequate.
I like to approach the exposure assessment in this way, because youâre basing it on an existing risk assessment. Plus, as part of the assessment, youâll have created a set of requirements for the LLM to satisfy before rollout.
To address AI risks, youâll also need user education and awareness [Clause 7.3 (âawarenessâ) and control 6.3 (âinformation security awareness, education and trainingâ)].
Behavioural economics and user education
Presumably, that also ties into behavioural economics. That people can make decisions 1) by taking shortcuts or 2) through thoughtful and detailed analysis â but they usually go for the shortcut, which makes them more likely to fall for an AI-powered scam.
With that in mind, what should user education look like? How might it be different from âtraditionalâ staff awareness?
Iâd roll out specific AI training to all users before they start using AI.
We need to educate users about how convincing AI can be. It can make up information thatâs internally consistent and entirely plausible.
Users must learn to always double-check the information against a verified source â even if it looks absolutely authoritative.
What about AI-powered phishing scams?
Phishing emails and scams are now incredibly convincing, because they can be fully tailored to the individual. The message can look as though it genuinely came from someone you know, and refers to information that person would have.
We need to teach people that just because something is written in your colleagueâs or friendâs style, doesnât automatically mean they wrote it. Thatâs very different to how we used to teach people to be wary of things like spelling and grammatical errors.
But you canât just rely on telling people to be ultra-super-cautious. Thatâs not what us humans excel at.
So, what do we tell people instead?
The answer lies in understanding human behaviour and psychology.
Rather than looking for specific âcuesâ in the message itself, which change over time anyway, look out for certain emotional reactions.
If you suddenly feel panicked, or feel like you need to take urgent action, thatâs your warning sign. The attacker is using a âhookâ on your psyche.
What about asking questions like âwhy would this person be asking this thing of me to begin withâ?
That falls under the old cues â looking out for things that seem a bit wonky. Itâs a âtellâ â but if we must assume that AI will become exceptionally good at not looking wonky, then youâd have to discount that, too.
That said, this particular âwonkinessâ remains effective because of the power imbalance. If your superior asks you to do something, even if it seems like an odd request, youâre more inclined to just do it.
But the most effective thing we can do is concentrate on the timeless characteristics of social engineering: asking ourselves how the message makes you feel.
As I said, if it makes you feel panicked, like you need to do something urgently, thatâs a clue that somethingâs off â regardless of the tools the messenger used to bring about that emotional reaction.
When that happens, stop. Slow down. Think. Get a second opinion. If your instinct tells you that something is wrong, listen to it.
Accounting for AI in a future edition of ISO 27001
Coming back to ISO 27001, in the latest version [ISO 27001:2022], one of the new controls was 5.23: information security for use of Cloud services.
But of course, the Cloud wasnât a new technology in 2022 or even 2013 [when the previous edition of ISO 27001 was published]. Rather, uptake of the Cloud ramped up in those intervening years, and comes with its own security challenges.
Are we going to see something similar for AI? That its uptake becomes so widespread that it needs its own control[s] in a future edition of ISO 27001?
I wouldnât be surprised to see precisely that. Not too long ago, ISO [International Organization for Standardization] even published an entire standard for AI. [ISO/IEC 42001:2023, providing the specification for an AIMS â an artificial intelligence management system.]
So, yes, itâs entirely possible weâll see one or more controls in the next version of ISO 27002, or Annex A of ISO 27001, that reference AI.
From the current version of ISO 27001, besides staff awareness [control 6.3], what are the top controls for protecting yourself from malicious use of AI?
Itâs really a case of looking through the controls and seeing what catches your eye.
Things like control 6.7 â remote working. This control might become very relevant if youâre not physically present with people, and it becomes difficult to check their identity.
So, it depends on the organisation?
Yeah. Itâs a bit like the Cloud â most controls in Annex A donât have the word âCloudâ in them, but theyâre still relevant to Cloud security. Or at least, they can be.
What other ISO 27001 requirements or controls should organisations think about in relation to AI risks and security?
Identifying your legal and regulatory requirements, and contractual obligations, as part of Clause 4.2 â thatâs definitely relevant, particularly if youâre an AI provider, with all these AI laws popping up.
Supply chain security [controls 5.19â5.22] is another interesting one. Think about intellectual property rights â whoâs got the copyright on AI?
Or control 5.35 â independent review of information security. Thatâs a handy control for AI penetration testing.
You can probably go through most ISO 27001 controls and find ways in which theyâre relevant to AI.
Learn more about the ISO 27001 controls
In her book, the second edition of ISO 27001 Controls, Bridget covers each Annex A/ISO 27002 control in detail, giving guidance on two key areas:
- Implementation â what to consider to fulfil the Standardâs requirements.
- Auditing â what to check for, and how, when examining the controls.
Ideal for information security managers, auditors, consultants and organisations preparing for ISO 27001:2022 certification, this book will help readers understand the requirements of an ISO 27001 ISMS.
About Bridget Kenyon

Bridget is the CISO for SSCL. Sheâs also been on the ISO editing team for ISMS standards since 2006, and has served as lead editor for ISO/IEC 27001:2022 and ISO/IEC 27014:2020.
Bridget is also a member of the UK Advisory Council for (ISC)2, and a Fellow of the Chartered Institute of Information Security.
Sheâs also been a PCI DSS QSA (Payment Card Industry Data Security Standard Qualified Security Assessor), head of information security for UCL, and has held operational and consultancy roles in both industry and academia.
Bridget is the sort of person whoâll always have a foot in both the technical and strategy camps. She enjoys helping people find solutions to thorny problems, and strongly believes that cyber and information security are fundamental to resilient business operations, not ânice to havesâ.
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