learn-ai-red-team-with-phoebe / Leader session 6 of 6
Learn AI Red Team with Phoebe · Leader track · Session 6 of 6

When to stop: "not a good use case for an LLM" is a finding

The last session of the leader track, and the one that gives you permission to use everything in the first five. If a workflow cannot tolerate the risk that remains after you have bounded it properly, the correct engagement outcome is to say so, in writing, and not ship it as an agent. This session grounds that in the UK NCSC's published position, hangs it on the governance hooks that already apply to you, looks honestly at how the vendor market handles disclosure, and closes the track with the four things a red-team report may actually claim.

🟠 Leader track Heads of security · eng leaders · risk and compliance 45 min
0-3 · Welcome 3-18 · The NCSC position and residual risk 18-40 · Governance, disclosure, and what you may claim 40-45 · Close
Part 0

The last session, and the line it does not cross

⚠ Authorization This course is about testing AI systems you own, or are contracted in writing to test. Every exercise runs against Beacon, a fictional company, inside a scope document written in the builder track. The course names attack and defence classes so a defender can build test cases. It contains no exploit payloads and teaches no attack craft. Testing a system you are not authorized to test is a crime in most jurisdictions, and no governance framework cited on this page changes that.
Not legal advice This session summarises published regulatory and standards material so that you know which instruments exist, roughly what they require, and which of your artefacts they touch. It is not legal advice, it is not a compliance opinion, and it is certainly not a determination of whether any obligation applies to your organisation. Applicability turns on your role in the value chain, your jurisdiction, your risk classification and dates that keep moving. Take the specifics to counsel, and take the quotations on this page to them as the starting point rather than the conclusion.

Five sessions of measurement have been building to a question that measurement cannot answer. Once you know the rate, know the blast radius, and know what your defences actually hold, somebody has to decide whether the remainder is acceptable. That is not a security decision. It is a business decision made by the person who owns the workflow, and the most useful thing this course can do is make sure that person is given a real choice, including the choice to decline.

Live - presented in session Self-study - read after class Official sources covered
★ What you walk out with today The NCSC framing in its own words, the sentence that turns "we should not build this" into a legitimate deliverable, the governance hooks that already require adversarial testing and its documentation, the published picture of how AI vendors handle disclosure, and the four-item list of what your report may claim - which is the closing artefact of the whole leader track.
Part 1 · the NCSC position

Prompt injection is not SQL injection, and that is a design instruction 8 min live

On 8 December 2025 the UK's National Cyber Security Centre published the clearest short statement any government body has made on this, and it is worth reading precisely rather than paraphrasing, because the precision is where the decision lives.

SQL injection: a fix exists Parameterised queries separate instruction from data at the interface. The boundary is enforced by the system, not inferred from the text. The fix removes the class. You mitigate once and stop measuring. Prompt injection: NCSC, 8 Dec 2025 "there's a good chance prompt injection will never be properly mitigated in the same way." "Under the hood of an LLM, there's no distinction made between 'data' or 'instructions'; there is only ever 'next token'." The instruction that follows, and it is the whole of session 6 "Rather than hoping we can apply a mitigation that fixes prompt injection, we instead need to approach it by seeking to reduce the risk and the impact. If the system's security cannot tolerate the remaining risk, it may not be a good use case for LLMs." UK NCSC Teach it as an outcome: "do not ship this workflow as an agent" is a finding, not a failure.
🔍 Click to zoom - why the SQL analogy breaks, and what the NCSC tells you to do instead

Two more lines from the same post are worth having in your head before the next architecture review. On deny-listing, the NCSC notes that "since LLMs are so complex there are infinite ways to rephrase an attack" - which is the reason a blocklist of known-bad phrasings is a maintenance burden rather than a control. And the "next token" line is not a rhetorical flourish. It is a statement about the mechanism, and it is why every attempt to make the model reliably distinguish trusted from untrusted text has to fight the way the system fundamentally works rather than a bug in it.

Notice what the NCSC does not say. It does not say do not use LLMs. It says reduce the risk and the impact, and then it says something that most vendor guidance carefully avoids saying: sometimes what remains is still too much.

LiveHow to make "do not ship this" a deliverable rather than an argument4 min▶

A recommendation to not build something lands very differently depending on how it arrives. Three things make it land as a finding rather than as obstruction, and all three are within your control as the person commissioning the engagement.

  • Write it in the same format as every other finding. Measured rate at a stated N, blast radius by data classification and by irreversible action, the mitigations tried, and the residual after each. A recommendation that arrives inside the finding template reads as the conclusion of the evidence. The same recommendation in an email reads as an opinion.
  • Offer the bounded version alongside it. Almost never is the answer "no AI here". It is usually "not as an autonomous agent with these permissions". Draft-and-approve instead of act. Read-only instead of write. A narrower data scope. The finding then presents a choice with two shippable options rather than a veto.
  • Name who decides. This is a risk-acceptance decision belonging to the business owner of the workflow, not to the red team and not to security. Your job is to make sure the residual risk is stated in terms that person can actually weigh, and that their acceptance is recorded. The failure mode is not that a business accepts risk. It is that nobody can say afterwards who accepted it or what they were told.

One more thing worth saying to an anxious team: this outcome is rare enough to be credible. Most engagements end with a bounded system and a set of controls. If your red team recommends against shipping on every second engagement, the problem is the red team. If it has never once recommended against shipping, the problem is also the red team.

Part 2 · governance hooks

Where adversarial testing is already written down 8 min live

Leaders funding this work usually need an external reason as well as an internal one. There is a better set of hooks available than most people realise, and one of them is unusually hard: it requires not just the testing but the documentation of it, which is precisely why the reporting template from session 3 has legal weight and not only operational weight.

The hooks that already apply, and the one that requires documentation. EU AI Act Article 15 - high risk Requires measures to prevent, detect, respond to, resolve and control for data and model poisoning, adversarial examples and model evasion, and confidentiality attacks. EU AI Act Article 55 - GPAI, systemic risk Applicable from 2 Aug 2025. Providers must conduct AND DOCUMENT adversarial testing, mitigate systemic risk, and report serious incidents to the AI Office without undue delay. Documentation is the hook. NIST AI RMF Playbook - the anchor for a programme rather than an exercise MEASURE 2.6: "Use red-team exercises to actively test the system under adversarial or stress conditions." MEASURE 2.7: "Establish and track AI system security tests and metrics (e.g., red-teaming activities, frequency and rate of anomalous events...)." The second one is what turns findings into a standing metric. CISA, NCSC-UK, NSA and 21 partners, Guidelines for Secure AI System Development: secure by design, with responsible release contingent on testing that includes red teaming, and continuous monitoring in operation. Singapore IMDA and AI Verify publish a starter kit naming benchmarking and red teaming as the two methods. Scoping trap: Article 15 sits in the high-risk chapter, while GPAI models are governed separately under Articles 51-56. At least one peer-reviewed analysis argues GPAI carries no equivalent explicit robustness obligation.
🔍 Click to zoom - four instruments, and the scoping trap between two chapters of the same act
★ Article 55 is the sentence to bring to a budget conversation For general-purpose AI models with systemic risk, applicable from 2 August 2025, providers must perform model evaluation including conducting and documenting adversarial testing, mitigate systemic risk, report serious incidents to the AI Office without undue delay, and ensure adequate cybersecurity. It is the clearest hard legal hook for adversarial testing anywhere today. Read the word documenting twice. An engagement that produced findings but no defensible written record satisfies neither the regulation nor the person who will have to explain it later.

The NIST pair is the other half, and it is the half that changes your operating model rather than your paperwork. MEASURE 2.6 gets you the exercise. MEASURE 2.7 gets you the programme: tests and metrics, tracked, with frequency and rate of anomalous events among the things you establish. A one-off engagement satisfies the first. Only a standing suite with a re-test trigger list satisfies the second, which is exactly what the builder track's final session builds.

The trigger list, since no standards body publishes a cadence No published standard names a re-test interval, and anyone quoting one to you is quoting a blog. Published practice is continuous automation plus event-triggered human rounds. The trigger list worth adopting: base-model version change, system-prompt change, new tool or MCP server, new connector or data source, new renderer, new user population or language, and any permission-scope change. Attach it to your MEASURE 2.7 metric and you have a defensible programme rather than a calendar reminder.
Part 3 · disclosure, and what you may claim

The market you are buying from, and the report you are signing 7 min live

Before the closing artefact, one piece of evidence about the ecosystem. Piao, Li and Woods at Edinburgh studied the vulnerability disclosure posture of 264 AI vendors, and the picture is worth having in front of you the next time somebody says a finding will be handled through the vendor's normal channel.

What they found across 264 AI vendorsThe numberWhy it matters to you
No disclosure policy at all36%More than a third have no published route for a researcher, or for you, to report a finding responsibly
Policies that mention AI risks18%Even where a policy exists, it usually describes classic software vulnerabilities and is silent on AI-specific behaviour
Most common out-of-scope itemsjailbreaking, hallucinationPrecisely the two categories your users will report to you first, and the two your vendor is least likely to accept
Posture split46 proactive · 115 silent · 103 restrictiveSilence is the modal posture. Restrictive is more common than proactive
Timinglater than research, later than incidentsVendors address AI vulnerability disclosure after the research community and after real incidents, not before

Two practical consequences. First, when you procure, ask for the disclosure policy and read whether it mentions AI at all; the answer is a reasonable proxy for how a serious finding will be received. Second, plan your own disclosure path before you need it, including the information-hazard question: a not-yet-known technique written up carelessly accelerates misuse of systems other than yours, which is one of OpenAI's own published limitations of red teaming.

Which brings the leader track to its closing artefact. Five sessions of measurement, evidence and governance exist to support exactly four sentences, and to forbid one.

What a report may claim - only these four things 1 · These specific attacks succeeded, at these measured rates, under these conditions, against this build at this date. 2 · These specific weaknesses and impacts exist, with these blast radii. 3 · These specific mitigations changed those rates by these amounts. 4 · These risk surfaces were explored, and these were not. What it cannot claim Safe. Secure. Robust. No amount of testing establishes that something cannot happen. The search space of natural-language attacks is effectively unbounded, and the attacker moves second. Absence of evidence, again. If a stakeholder wants the word "safe", the correct answer is the NCSC's Reduce the risk and the impact. If the system's security cannot tolerate the remaining risk, it may not be a good use case for an LLM. That sentence is the honest end of a leader track, and it is a decision leaders make.
🔍 Click to zoom - the closing artefact of the leader track, in four claims and one refusal
In the vendors' own words

You are not asking for a standard nobody meets. The people who build these systems say the same thing about their own evaluations. OpenAI's system card: "evaluations represent a lower bound for potential capabilities; additional prompting or fine-tuning, longer rollouts, novel interactions, or different forms of scaffolding could elicit behaviors beyond what we observed." Anthropic: no system is completely immune to all attacks. Microsoft: it is still possible that some injections might evade these defences, and the idea that it is possible to guarantee or solve AI safety through technical advances alone is unrealistic. If a supplier's marketing is more confident than the frontier labs' own documentation, that gap is itself a finding.

Discussion 1 of 2

Run the stop decision on Beacon's Support Bot ★ 10 min · in threes

Beacon's engagement is finished. The Support Bot reads inbound customer email, holds access to account records, and can issue refund credits. The measured findings are on the table and the board review is on Thursday. Decide, as a group, what the report recommends, and be able to defend it in the language of Part 1.

State the residual, not the fear. Write the remaining risk as a sentence with numbers in it: this class succeeded k of N times against this build at this date, reaching this data classification and this set of irreversible actions, with these mitigations in place. If your group cannot write that sentence, the decision is premature and the finding is "we do not yet know", which is also a legitimate output.

Try the bounded versions before the refusal. Draft-and-approve instead of act. Read-only credentials with refund issuance behind a human. A narrower retrieval scope so the bot never sees records outside the requesting customer's account. Each of these is a different product, with a different residual. Price at least two before recommending against any.

Now ask the NCSC question directly. Can Beacon's security tolerate what remains, given that no mitigation on the table removes the class? If yes, the recommendation is ship with these bounds and this monitoring. If no, the recommendation is do not ship this workflow as an agent, and that is a finding.

Name the accepter and record the acceptance. Whoever owns the workflow accepts the residual, in writing, having been told the numbers. This is the artefact that makes the difference eighteen months later when somebody asks how this was allowed. Do not let the security team be the accepter by default, which is what happens when nobody is named.

Where groups usually go wrong They debate whether the risk is acceptable before anyone has written the residual as a measured sentence, and the discussion becomes a contest of confidence rather than a reading of evidence. Insist on the sentence first. The decision is often obvious once it exists, and the times it is not obvious are the times a business owner genuinely should be the one deciding.
Discussion 2 of 2

Audit one report you have already signed ★ 8 min · in pairs

Bring the most recent AI security assessment, penetration test or assurance summary your organisation has accepted. In pairs, run it against the closing artefact. This is uncomfortable by design, and it is the fastest way to make the four claims stick.

Highlight every sentence that asserts a property rather than a measurement. "The system is secure against prompt injection" is a property. "This attack class succeeded 3 of 25 times against build 4.2 on 14 August" is a measurement. Count both. The ratio tells you what kind of document you signed.

Find the fourth claim, which is the one almost always missing. Which risk surfaces were explored, and which were not? A report without an explicit not-tested list invites the reader to assume the tested set was complete, and the accounting rule from the builder track is that an untested class counts at full inherent risk. The board hears "unknown", never "safe".

Check whether N appears anywhere. If findings are binary rather than k of N, the reliability of every one of them is unknown, and severity decisions made on top of them inherited that gap.

Decide what you will require next time, and write it into the engagement brief rather than into a review comment on the draft report. The three requirements that fix most of this: state N, state which endpoints were tested, and include the not-tested list.

Closing the track Six sessions, and the through-line has not changed since session 1: you cannot make the model refuse to be fooled, you can bound what being fooled gets an attacker, and you can report honestly on both. If you want the mechanics - writing the rules of engagement, mapping the surface, building the suite, running the engagement, hardening and retesting - the builder track starts at the bottom of this page.
Homework

Try it yourself - this week ◐ 45-60 min total

Source material

Official sources covered

Every framework, figure and quotation on this page traces to a primary source catalogued in this course's source map, verified 2026-08-14. Regulatory material is summarised, not interpreted, and this page is not legal advice. This page covers:

✓UK NCSC, 8 Dec 2025 - prompt injection is not SQL injection, the "next token" statement, deny-listing, and "it may not be a good use case for LLMs"Part 1 · [P] · quoted verbatim
✓EU AI Act Article 15 - prevent, detect, respond to, resolve and control for poisoning, adversarial examples and confidentiality attacksPart 2 · [P] · high-risk chapter
✓EU AI Act Article 55 - GPAI with systemic risk, applicable from 2 Aug 2025, conducting AND documenting adversarial testingPart 2 · [P] · the clearest hard legal hook today
✓NIST AI RMF Playbook MEASURE 2.6 and MEASURE 2.7Part 2 · [P] · the compliance anchor for a standing programme with metrics
✓CISA / NCSC-UK / NSA and 21 partners, Guidelines for Secure AI System Development (Nov 2023)Part 2 · [P] · secure by design, release contingent on testing including red teaming
✓Singapore IMDA / AI Verify, Starter Kit for Safety Testing of LLM-Based ApplicationsPart 2 · [P] · names benchmarking and red teaming as the two methods
✓Piao, Li and Woods (Edinburgh) - 264 AI vendors, 36% no disclosure policy, 18% mention AI risks, 46 / 115 / 103 posture splitPart 3 · [P] · jailbreaking and hallucination most commonly out of scope
✓What a report may claim - the four claims, and the refusalPart 3 · course closing artefact · assembled from the primary sources across the track
✓Vendor statements: OpenAI system card lower-bound language, Anthropic, Microsoft on guaranteeing AI safetyPart 3 · [P] all three
✓OpenAI's published limitations of red teaming - information hazards and point-in-time relevancePart 3 · [P]
◐The Article 15 versus Articles 51-56 scoping questionPart 2 · at least one peer-reviewed analysis argues GPAI carries no equivalent explicit robustness obligation · summary only, take it to counsel
◐Re-test cadencePart 2 · no standards body publishes an interval · the trigger list is published practice, not a standard
Check yourself

Three questions before you go 🎯 ◐ 90 seconds

1 · The NCSC writes that if the system's security cannot tolerate the remaining risk, it may not be a good use case for LLMs. How should an engagement treat that sentence?

Option A is contradicted by session 5's evidence: the layers reduce a rate and the stack in LLMail-Inject still let one attempt in six through. Option B moves the decision to somebody who cannot see your blast radius. The whole point of the NCSC framing is that the remaining risk is measured on your side of the boundary, and the decision belongs to the person who owns the workflow. Making the refusal a properly formatted finding, with bounded alternatives, is what stops it reading as obstruction.

2 · Which governance hook most directly explains why your reporting template matters legally rather than only operationally?

All three are real hooks and all three are worth citing, but only Article 55 attaches an explicit documentation obligation, which is what converts a good engagement into a defensible record. Note the scoping trap that goes with it: Article 15 sits in the high-risk chapter while GPAI models are governed separately under Articles 51-56, so which chapter applies depends on your role in the value chain. That is a question for counsel, not for a slide. MEASURE 2.7 is the other one to remember, because tracking tests and metrics is what makes a programme rather than an exercise.

3 · A stakeholder asks you to write that the system is secure against prompt injection. What may the report actually say?

Options A and C are the two ways this goes wrong in practice, and C is the more seductive because the caveat sounds rigorous. Neither survives the fact that no amount of testing establishes that something cannot happen. Option D quietly substitutes a decision for a measurement: risk appetite is the business owner's judgement about a stated residual, not a property your report can assert. The fourth claim is the one most reports omit, and omitting it lets the reader assume the tested set was complete. If a stakeholder still wants the word, the honest reply is the NCSC's: reduce the risk and the impact, and if the security cannot tolerate what remains, it may not be a good use case for an LLM.

Leader session 6 cheat sheet · pin this

NCSC, 8 Dec 2025SQL injection can be properly mitigated with parameterised queries; there is a good chance prompt injection never will be, in the same way.
There is only ever "next token"Under the hood there is no distinction between data and instructions. That is the mechanism, not a bug to be patched.
Deny-lists loseSince LLMs are so complex there are infinite ways to rephrase an attack. A blocklist is maintenance, not a control.
"Not a good use case" is a findingReduce risk and impact; if security cannot tolerate the remainder, do not ship the workflow as an agent. Write it in the finding template, price the bounded alternatives, name who accepts.
EU AI Act Art. 55GPAI with systemic risk, from 2 Aug 2025: conduct AND DOCUMENT adversarial testing, mitigate, report serious incidents to the AI Office. Documentation is why the template matters legally.
Art. 15 vs Arts. 51-56Article 15 is the high-risk chapter; GPAI is governed separately. Which one applies depends on your role. Summary only, not legal advice.
MEASURE 2.6 and 2.72.6 gets you the exercise. 2.7 gets you tracked tests and metrics, which is the standing programme. No standards body publishes a cadence, so use the trigger list.
The four claims, and the refusalRates under conditions against a build · weaknesses with blast radii · what the mitigations changed · what was and was not explored. It cannot claim safe, secure or robust.