A CEO's Nightmare: How £20 Million Became £0

February 1st, 2025, was shaping up to be a terrible day for the CEO of Excellorate Technologies, Paul Maddox. But he didn’t know it yet. The morning started like any other—an espresso at his marble kitchen counter, a glance at the Financial Times, and a glance at the still-dark London skyline from his glass-walled penthouse.

His executive assistant had sent the usual briefing: meetings with the board, updates on the latest round of redundancies, and a few unread emails flagged “urgent.” Maddox had a nagging sense that one of those emails would ruin his week. He just didn’t expect it would ruin his career.

By 9:00 AM, he was sitting in his corner office on the 32nd floor of a gleaming, expensive tower in the City of London. The early morning glow cast long shadows through the office’s open space. There was an air of serenity about the place, a calm before the storm. Then, the phone rang. It was Samantha, his COO, sounding unusually tense.

“We’ve got a problem,” she said curtly. “It’s MunicRe. They’ve denied our £20M claim for the ransomware attack last month.”

Maddox froze. This couldn’t be right. The cyberattack had crippled Excellorate’s systems for over a week. It had been one of the most sophisticated attacks their IT department had ever seen. They’d immediately filed a claim under their comprehensive Cyber and Data Insurance policy, expecting their multimillion-pound coverage to kick in. This insurance was their safety net. No one had anticipated the kind of liability now staring them in the face.

“They what?” Maddox asked, his voice low and dangerous.

“They’ve denied it. Completely.”

It was like a switch flipped in his brain. His hands shook as he opened his inbox. Sure enough, there it was: an email from Dr. Jokke Wenn, Claims and Compliance Director at MunicRe Insurance. The subject line read: “RE: Excellorate Technologies Ransomware Incident – Claim Denial.” He clicked on it, eyes darting through the cold, legalistic text.

“Further to your £20M claim for your ransomware incident, dated 1st February 2025, against your Cyber and Data Insurance policy, we regret to inform you that your non-compliance with your policy conditions means that we are not liable in this instance…”

Maddox’s heart sank as he read on. Non-compliance with Regulation (EU) 2022/2554, otherwise known as the Digital Operational Resilience Act (DORA). Failure to meet obligations under What is not covered: 3. Failure by service providers. And the list continued: Pre-existing problems. Fines, penalties, and sanctions. Non-specific privacy investigations.

His mind raced, desperately searching for an escape. Hadn’t their compliance team assured him they were fully aligned with DORA? That they had mitigated every risk, covered every base? Now, out of nowhere, this obscure regulation from the EU was about to cost them £20 million—and potentially far more.

He dialed Samantha back immediately.

“We’re not non-compliant with DORA, are we? We’ve covered that,” he blurted out before she could even say hello.

There was a pause.

“Well, Paul, that’s the thing. We thought we were compliant. But the investigation turned up some discrepancies. Apparently, our third-party provider didn’t meet the required security standards under DORA. And there were issues with our internal audits. They’re saying it counts as a pre-existing problem.”

Maddox clenched his jaw. A pre-existing problem? This sounded like legal nonsense. MunicRe was using every loophole to avoid paying. But Samantha’s next words landed like a gut punch.

“Paul, they’re also saying that this denial might affect our eligibility for future policies. We’re at risk of being uninsurable.”

Uninsurable.

It was one thing to lose the £20M payout. That would be painful, sure, but the company could survive it. But being uninsurable in the current landscape? It would be a death sentence. Excellorate’s clients, particularly in the financial sector, would never stay with a firm that couldn’t demonstrate airtight cybersecurity and a robust insurance fallback. It would be like wearing a neon sign that said: Vulnerable to cyberattack.

“I’ll deal with this,” Maddox said through gritted teeth, hanging up before Samantha could respond.

By noon, the boardroom was in chaos. Excellorate’s senior executives were seated around the table, while Maddox paced like a caged animal. They were all there—Samantha, the CFO Adrian, the Chief Legal Officer Julian, and a few other department heads. Their faces were ashen.

“We need that money,” Adrian said bluntly, breaking the tense silence. “Without it, we’re looking at a liquidity crisis. Not tomorrow, but soon. Our investors won’t sit tight if they smell blood.”

“I know,” Maddox snapped. “Do you think I don’t know that?”

Samantha, always the calm voice of reason, was trying to explain how they could negotiate with MunicRe. “We might be able to appeal. If we can prove that our non-compliance didn’t directly lead to the attack, we could—”

“An appeal will take months, and we don’t have months!” Maddox interrupted, slamming his fist on the table. The room fell silent again.

Julian, who had been quietly reviewing the insurance policy, cleared his throat. “Paul, I’ve looked over their decision. It’s airtight. There’s no wiggle room. They’re relying on DORA, and it’s clear that we dropped the ball with our third-party vendor. We didn’t audit them properly, and now we’re paying the price.”

Maddox turned to him, seething. “So, you’re saying we just eat the loss? A £20 million loss?”

Julian held his gaze. “I’m saying we can’t rely on MunicRe to save us. We need to find another way.”

That evening, back in his office, Maddox stared out the window, the city lights twinkling below him. The same thought kept looping in his mind: How did we let this happen?

Excellorate had always been one step ahead, always outmaneuvering the competition. But they had grown complacent. DORA, SS1/21, SS2/21—all these regulations had seemed like red tape, bureaucratic hurdles to jump through, rather than existential threats. Now, they were at the center of the storm.

His phone buzzed. It was an email from the Prudential Regulatory Authority (PRA), referencing Supervisory Statements SS1/21 and SS2/21, along with a notice of investigation. The timing was impeccable, he thought bitterly. Regulatory fines would be the least of his worries now. Excellorate would be hit with penalties, that much was certain. But the real danger lay in what was coming next.

If clients got wind of the fact that Excellorate’s cyber insurance claim had been denied—if they found out that the company had been non-compliant with DORA—they would flee. A mass exodus. Contracts worth millions of pounds would vanish overnight. Excellorate’s reputation, once stellar, would be irrevocably tarnished.

And then there was the question of his own future. The board wouldn’t forgive this. Investors wouldn’t either. Maddox had made them believe in the illusion of invincibility—until today.

How did we let this happen?

He knew the answer. They had gambled, cutting corners on compliance, trusting that their insurance would be the safety net. They had relied on half-baked audits, pushed off responsibility onto third-party providers, and now, they were going to pay for it. Dearly.

His phone rang again. This time, it was Samantha.

“Paul,” she said quietly. “We need to talk. The clients are starting to ask questions. They want reassurance.”

Maddox swallowed hard, already dreading the conversations ahead.

By the end of the week, Excellorate’s stock had plummeted by 30%. Maddox had been summoned to an emergency board meeting—this one without him in the chair.

His reign was over.

The £20 million? Gone. His reputation? In tatters.

And the worst part? It could all have been avoided if they’d just taken compliance seriously.

In the world of high-stakes business, it turns out, it’s not the cyberattacks that kill you.

It’s the fine print.