Give targeted support, adjust the scenario mix, and review whether the user’s work context is increasing susceptibility. Repeated failure is not only a training problem; it can also show that the organisation needs better message realism, clearer reporting paths, or more context-aware intervention.
Why repeat phishing failures need a broader response
Repeat failure is a signal, not just a score. If the same users keep missing phishing simulations or real messages, organisations should treat that as evidence that the intervention is not matching the user population, the working environment, or the realism of the scenario set. The goal is not to punish mistakes, but to change the conditions that make the mistakes likely.
That usually means moving beyond generic awareness content. Users who are time-pressured, overloaded, frequently interrupted, or working in roles that handle external email all day may need different support than someone who rarely touches suspicious messages. When the same pattern persists, the organisation should assume the current approach is underfitted to the actual risk context.
A useful way to think about this is that phishing resilience is partly behavioural and partly operational. Message realism, reporting friction, and job context can matter as much as knowledge. In practice, Dropbox GitHub breach 2022 and Mailchimp breach 2022 both show how social engineering succeeds when message legitimacy and internal trust are strong enough to bypass caution.
How to adjust the intervention when failures repeat
Start by segmenting the users who are failing. A repeated miss does not mean every user needs the same corrective action. Some users may need contextual coaching, some may need a different scenario mix, and some may need workflow changes because the messages they receive are difficult to distinguish from real business traffic.
Then vary the simulation content. If every exercise is too obvious, users learn the pattern rather than the lesson. If every exercise is too advanced or too synthetic, the organisation measures curiosity or guesswork instead of real-world susceptibility. The scenario set should reflect the organisation’s actual mail flows, approval chains, and supplier interactions so that the exercise is testing judgement in context, not memory of a training template.
Reporting paths matter too. If users do not know exactly how to report suspicious mail, or if reporting feels slow and unrewarded, repeated failure becomes more likely. Organisations should make the safe action simpler than the risky one, and they should verify that the reporting path works on the devices and channels people actually use. The control should reduce exposure, not just record mistakes.
The underlying lesson is similar to what we see in Ledger Connect Kit npm compromise 2023 and Solana web3.js npm compromise 2024, where trust in a familiar path or a familiar actor became the opening attackers needed.
What good looks like after you change course
Good practice is not a perfect phishing score, it is a measurable reduction in repeat susceptibility and a faster, cleaner reporting response. Organisations should look for evidence that users who previously failed are now improving, that reports are arriving earlier, and that the organisation can explain why certain groups were more exposed than others.
Good outcomes usually include three things: fewer repeat failures in the same cohort, more accurate reporting from the first contact, and better alignment between scenario difficulty and role context. If those signals do not move after targeted support, the problem may be less about awareness and more about workflow design, mail volume, or unrealistic expectations about how people work under pressure.
Where phishing failures connect to credential theft or token abuse, the organisation should also check whether the wider control environment is absorbing the lesson. EmeraldWhale Git config credential theft and CoPhish OAuth phishing via Copilot Studio show why phishing resilience has to be measured against real downstream access, not just click rates.
Risk and Threat Considerations
repeat phishing failure increases the chance that a real attacker will find a user group that is both reachable and persuadable. The risk is not only that someone clicks, but that they also disclose credentials, approve access, or miss the reporting window that would let defenders contain the event quickly.
Failure mechanism: The same situational cues keep working because the organisation has not changed the user’s decision environment, so the attacker can reuse familiar formats, timing, and trust signals until one message lands.
Impact: Repeated susceptibility can raise the probability of account compromise, business email compromise, token theft, or follow-on fraud, and it can weaken confidence in the organisation’s ability to spot and interrupt the attack path early.
Standards & Framework Alignment
This section maps relevant standards and security frameworks to the operational risks and controls described in this guidance.
CIS Controls v8, NIST CSF 2.0 and NIST SP 800-53 Rev 5 set the governance and control requirements practitioners need to meet.
| Framework | Control / Reference | Relevance |
|---|---|---|
| CIS Controls v8 | CIS-14 — Security Awareness and Skills Training | Repeat phishing failures are directly addressed by awareness training and phishing tests. |
| Recommendation — Tailor phishing training to observed failure patterns and role-specific exposure. | ||
| NIST CSF 2.0 | PR.AT-01 — Awareness and Training | The issue concerns improving user awareness and response to phishing attempts. |
| RS.CO-02 — Incident Reporting | Phishing resilience depends on clear, usable reporting paths for suspicious messages. | |
| Recommendation — Use role-based awareness content and phishing exercises to reduce repeat susceptibility. Make suspicious-message reporting simple, tested, and widely understood. | ||
| NIST SP 800-53 Rev 5 | AT-2 — Awareness Training | Repeat failures indicate training content and targeting need adjustment. |
| IR-6 — Incident Reporting | Users must know how to escalate suspicious messages quickly and reliably. | |
| Recommendation — Provide targeted awareness training that reflects actual phishing exposure and job context. Verify that reporting procedures for phishing are clear and usable in practice. | ||
Practitioner Guidance
What to prioritise: Treat repeat failure as a triage signal. Focus first on the users and roles with the highest exposure, the most realistic lures, and the weakest reporting behavior, rather than resetting the same generic training for everyone.
What to verify: Check whether the scenario library matches current business communications, whether the reporting route is obvious and tested, and whether failed users are being measured against a realistic benchmark for their role. If those three are not aligned, the program will keep misreading the problem.
Decision rule: If the user is failing in a high-volume, high-interruption role, prefer targeted intervention and workflow adjustment over more frequent punishment-style simulations. If the same user fails after the process is simplified, escalate for a deeper review of role context and control design.
Practitioner takeaway: Repeat phishing failure is often a control-design problem wrapped in a training metric, so the right response is to tune the scenario, the reporting path, and the user context together.