Cloudflare Outage Exposed Stuff We Miss – Ep 538 

Ever wondered what really keeps the Internet running – and what happens when it all goes sideways? The latest Cloudflare outage served up a reality check, exposing just how much of our digital world hangs together with a mix of duct tape, toothpicks, and a whole lot of hope. In this episode we dive into how this outage sent shockwaves through everything from simple website clicks to healthcare payment systems, and why most folks had no idea Cloudflare was even a linchpin for their daily operations.

In this episode:

Cloudflare Outage Exposed Stuff We Miss – Ep 538

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Cloudflare Outage Exposed Stuff We Miss

We’re pulling the technical breakdown from a couple of articles by HealthcareInfoSecurity and the other is the same topic using a resilience-testing angle from Brian Krebs’ piece, where he quoted Nicole Scott making the case for treating this outage like a TTX.

Breach Roundup: Cloudflare Outage Root Cause – BankInfoSecurity

The Cloudflare Outage May Be a Security Roadmap

What is Cloudflare?

• Speeding up websites using their global network getting you to information via the quickest route possible..
• Protecting sites from attacks, like DDoS attacks that can overwhelm servers. They are hit constantly but still manage to fend off the attacks and keep things running smoothly. They were attacked by a bot network in 2019 that shut down a bunch of sites until they could stop it. That was the last time there was a major issue like this.
• Acting as a content delivery network (CDN) that stores copies of website data closer to users. That means they make sure you get a copy of the website you are asking to see by accessing the closest server to you so content loads quickly. It also explains why sometimes the data may be slow to update.
• Providing security tools such as firewalls, bot protection, and encryption.
• They also provide some DNS features that are more complex than other hosts will provide.

In short, Cloudflare sits between a website and the rest of the internet. It is there because it is supposed to keep things fast, secure, and reliable. But when that goes wrong…….

[07:56]”] What happened

• Cloudflare changed a database query in its bot-management system.
• That change caused a key file to double in size — too big for Cloudflare’s systems to process efficiently.
• Because the file was too large, Cloudflare’s edge servers kept flipping between good and bad versions of it every few minutes.
• This caused global instability and outages.
• Cloudflare emphasized it was not a cyberattack, just an internal glitch.
• They classified it as their worst outage since 2019.
• Donna-friendly analogy: “Their bot bouncer tried to handle a guest list twice as long and basically fainted at the door.”

[16:05]”] The tabletop exercise idea

• This perspective comes from Nicole Scott, quoted in Brian Krebs’ article.
• She explains that outages like this reveal how much organizations rely on Cloudflare as a protective shell.
• Many developers assume Cloudflare’s WAF and bot filtering will block common attacks — so they don’t build strong security directly into their apps.
• When Cloudflare goes down, those protections vanish.
• Her point:
“This outage was basically a free tabletop exercise. You just learned what breaks when Cloudflare isn’t there to save you.”
• Krebs highlights the same angle — outages expose dependency risks and operational shortcuts.

[24:01]”] Real-world healthcare impact

• One of our clients learned the hard way that Cloudflare isn’t just a “web protection thing.”
• Their payment system for all clinics depended on Cloudflare.
• When Cloudflare went down, they couldn’t take credit cards anywhere.
• Every clinic lost the ability to process copays and card payments — immediate revenue impact and front-office chaos.
• The scary part: the client had no idea Cloudflare was part of their vendor’s payment workflow.

So, be glad if you didn’t know about Cloudflare already because that means you didn’t suffer the outage impacts. But, use what we discussed to do a tabletop exercise even if you weren’t affected. The next time, you could be the one trying to get the squirrels to stop chewing the power lines.

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