Sample Scenario — Retail Data Breach Simulation

The Larkin & Co. Card Breach Exercise

A branching, choose-your-path tabletop built for a national retailer. Someone has been quietly copying card numbers from the checkout page for five months, and the biggest shopping week of the year starts in four days. Six shared injects establish the breach, then the room's own decision — take checkout offline, or keep selling while forensics works — sends the exercise down one of two independent, fully-scripted paths. Neither one saves the holiday.

16injects per path
2diverging paths
10 dayssimulated timeline
3.5 hrstypical runtime

Fictional, but built to feel real in the room.

Every detail below is fictional — specific enough to feel real in the room, and generic enough to map onto almost any business that takes payments online through a site built from dozens of third-party components.

Larkin & Co.

A Denver-based outdoor and apparel retailer with 310 stores, ~14,000 employees, and $3.6B in annual revenue. E-commerce makes up 42% of sales, and the five days from Black Friday through Cyber Monday account for nearly a fifth of the year's online revenue.

Larkin's checkout page is its own, but the code running on it isn't all Larkin's. Like most retail sites, it loads dozens of third-party scripts — analytics, personalization, reviews, chat. Any one of them can see what a customer types. Nobody at Larkin owns the full list.

Online checkout — 42% of revenue, holiday peak in four days
Brightpath Analytics — third-party analytics script vendor
Acquiring bank — card processing, enforces card network rules
Customers — about 900,000 cards potentially exposed

The crisis everyone faces.

Six injects, delivered over the first 47 hours, that every player experiences regardless of what the room ultimately decides. This phase ends with the decision that splits the exercise in two.

DAY 0
10:00
INJECT 1Detection

A common point of purchase

Larkin's acquiring bank calls: card networks have flagged Larkin as a likely "common point of purchase" for a cluster of fraudulent transactions. The bank wants a response by end of day.

Tests: how a breach notification from a third party is escalated — and who takes the call seriously.
15:00
INJECT 2Scoping

A script that shouldn't be there

Security finds unfamiliar code on the checkout page, loaded through a compromised script from Larkin's analytics vendor. It has been sending card numbers to a lookalike domain since June. Up to 900,000 cards may be affected.

Tests: scoping a breach that lives in the browser, outside the systems security usually watches.
DAY 1
09:00
INJECT 3Commercial

Four days to Black Friday

Black Friday is four days away. The merchandising team projects $210M in online sales over the five-day holiday weekend, and inventory has been bought to match.

Tests: how commercial pressure shapes a security decision — and who's in the room when it does.
12:00
INJECT 4Payments

The card network rules

The acquiring bank tells Larkin it must engage an approved forensic investigator, and that card network fines and assessments are likely. The size will depend in part on how long the exposure continues.

Tests: understanding obligations you agreed to in a contract most executives have never read.
15:00
INJECT 5Third party

"Your tags, your responsibility"

Brightpath Analytics denies it was breached and says customers are responsible for the scripts they place on their own sites. It declines to share its logs without a subpoena.

Tests: third-party accountability when the vendor's contract was written by the vendor.
DAY 2
09:00
INJECT 6Decision point

Take checkout offline, or keep selling

Security can remove the malicious script within the hour. But forensics can't confirm the site is clean for three to five days. The room has two options: take online checkout offline until a clean rebuild is verified — losing most of Black Friday — or remove the script, add monitoring, and keep selling while forensics works. The room has to decide.

Tests: a security decision with a nine-figure revenue impact, made before the facts are in. This is the fork.

The room decides. The exercise branches.

INJECTS 1–6 DECISION A — GO OFFLINE B — KEEP SELLING

From here, the facilitator runs one of two fully independent scripts depending on what the room chose in Inject 6. Toggle between them below to see how each one unfolds — in a live session, players only ever see the one they earned.

Path A — the room takes checkout offlineTen injects. Going offline protects customers, not the quarter — and "checkout unavailable" the week of Black Friday says more than you mean it to.
DAY 2
13:00
INJECT 7ACustomers

"Checkout temporarily unavailable"

Larkin takes online checkout offline and posts a maintenance message. Within hours, customers and tech bloggers speculate about a breach. Larkin's social media team has no approved response.

Tests: communications when your silence is being interpreted for you.
DAY 3
10:00
INJECT 8AStores

Everyone goes to the store

Shoppers redirect to stores. Online-only inventory sits in distribution centers, store staffing was planned for a normal week, and in-store pickup orders are stuck in a system that's also offline.

Tests: the operational knock-on effects of a decision made for security reasons.
16:00
INJECT 9AMedia

Disclosure, sooner than planned

A reporter calls asking whether the outage is a breach. Counsel advises that Larkin should confirm it rather than issue a misleading denial — days before notification letters are ready.

Tests: disclosure timing when the decision is made for you by a reporter's question.
DAY 4
09:00
INJECT 10AFinancial

Black Friday, without the website

Online sales on Black Friday are down about $140M from plan. The CFO recommends lowering quarterly guidance, and the CEO has an investor conference next week.

Tests: investor communications when a responsible decision has a visible cost.
DAY 5
11:00
INJECT 11AForensics

The second skimmer

Forensics finds a second piece of skimming code inside the mobile app's embedded checkout. It would have kept collecting card numbers if Larkin had simply removed the first script and kept selling.

Tests: how a finding that justifies a costly decision gets communicated — and to whom.
DAY 6
10:00
INJECT 12ANotification

870,000 letters

Forensics confirms about 870,000 cards were exposed. Notification emails start going out, and customers' email providers flag many of them as phishing.

Tests: notification mechanics that work in practice, not just on paper.
DAY 7
14:00
INJECT 13APayments

The assessment

The card networks signal that fines and fraud assessments could reach about $11M. The acquiring bank wants a remediation plan within 30 days.

Tests: negotiating with parties whose rules you agreed to but didn't write.
DAY 8
09:00
INJECT 14ADecision point

Relaunch for Cyber Monday?

Engineering has rebuilt checkout with far fewer third-party scripts. Forensics has validated most of it, but not all. Relaunching now captures Cyber Monday; waiting three more days means full validation. The room has to decide.

Tests: how much residual risk the room will accept, and whether the answer changed now that the revenue is real.
DAY 9
11:00
INJECT 15AVendor

No security terms

Counsel reviews the Brightpath contract: it has no security requirements, no right to audit, and a liability cap equal to three months of fees. Larkin has 41 similar script vendors.

Tests: third-party risk management for vendors nobody thought of as critical.
DAY 10
10:00
INJECT 16ARemediation

Who owns the checkout page?

The post-incident review finds that marketing, e-commerce, and security each assumed someone else was approving the scripts on the checkout page. Nobody was.

Tests: separating the immediate response from the ownership gap that made the breach possible.
Path B — the room keeps sellingTen injects. Staying open protects the quarter, not the customers — and every hour of exposure is one the room chose.
DAY 2
12:00
INJECT 7BContainment

Script removed, monitoring on

The malicious script is removed, and security adds monitoring for unexpected changes on checkout. Sales continue normally. The decision rationale is captured in a single email thread.

Tests: whether the decision to keep selling is documented well enough to defend later.
DAY 3
15:00
INJECT 8BForensics

The second skimmer

Forensics finds a second skimmer, hidden inside the mobile app's embedded checkout. It has been active the whole time — about 30 more hours of peak-season traffic, and roughly 60,000 more cards.

Tests: responding when the decision to stay open turns out to have extended the harm.
18:00
INJECT 9BPayments

Continued exposure

The acquiring bank escalates: continued exposure after Larkin knew of the breach will likely increase card network assessments. The bank asks Larkin to confirm in writing when the exposure ended.

Tests: what you can truthfully put in writing about when you knew what.
DAY 4
08:00
INJECT 10BCommercial

A record Black Friday

Black Friday online sales beat last year's. At the same time, the fraud team sees rising chargebacks and card-not-present fraud linked to Larkin cards.

Tests: holding two truths at once: the business is up and the customers are being harmed.
15:00
INJECT 11BMedia

A researcher finds it first

An independent security researcher publishes a teardown of the skimmer found on Larkin's mobile checkout. Tech media pick it up within the hour, before Larkin has said anything publicly.

Tests: communications when someone else breaks your story with technical detail.
DAY 5
09:00
INJECT 12BDisclosure

"They kept selling"

Larkin confirms the breach. The coverage focuses on one fact: Larkin knew about the skimming before Black Friday and kept selling.

Tests: owning a decision publicly, including the part that looks worst.
DAY 6
14:00
INJECT 13BRegulatory

Attorneys general

Several state attorneys general send letters asking when Larkin learned of the breach, why it kept online sales open, and how many customers were affected after that date.

Tests: consistent, documented answers to the question you least want to answer.
DAY 7
11:00
INJECT 14BEmployees

The store associates hear it first

Store associates report being confronted by angry customers about the breach. They have no talking points, and some have posted their frustration on social media.

Tests: equipping front-line employees who absorb the reputational impact first.
DAY 8
09:00
INJECT 15BDecision point

How far does the remedy go?

Card fraud is generally reimbursed by issuing banks, so customers may not lose money directly. The room must decide whether to offer all affected customers identity monitoring and a goodwill credit — about $9M — or provide only what's required. The room has to decide.

Tests: whether the remedy is shaped by obligation or by what the company needs to rebuild trust.
DAY 10
10:00
INJECT 16BGovernance

Why did we keep selling?

The board asks to see the decision record from Day 2. It's a single email thread with no risk assessment attached. The board asks who made the call and on what basis.

Tests: decision documentation as a governance control, not an afterthought.

What the debrief surfaces.

The two paths are built to converge on the same hard questions, arrived at from opposite directions.

If the room took checkout offline

  • Was the cost of going offline weighed against a clear view of continued exposure — or against an assumption?
  • Who owned communications in the gap between going offline and being ready to disclose?
  • Who owns the list of third-party scripts on the checkout page — and who approves changes to it?

If the room kept selling

  • Was the decision to keep selling documented with a risk assessment and an owner at the time?
  • How was "the site is clean" defined, and who was accountable for confirming it?
  • Did the remedy offered to customers reflect obligation, or the trust the company needed to rebuild?
Larkin & Co., Brightpath Analytics, and all named details in this scenario are fictional and created for exercise purposes only.

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This is one scenario. Yours would be built around your business.

The Larkin exercise is a sample — built to show how a retail data breach simulation can branch on the decision that actually matters, and stay uncomfortable in both directions. A simulation built for your organization starts with your customers, your payment flows, and your peak season.

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Exercises often require access to crisis plans, escalation structures, and vulnerabilities. That material is handled in confidence, and NDAs are available on request.

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