Small businesses like ChadGPT can’t live without Cloudflare
On November 18, 2025, a large chunk of the internet went dark for a few hours — including ChadGPT.
Cloudflare, the infrastructure provider that sits in front of roughly one in five websites, had a self-inflicted software failure. A database permission change caused Cloudflare’s Bot Management system to generate a configuration file that unexpectedly doubled in size, hit a coded size limit, and triggered a latent bug in the core proxy software. That faulty configuration spread across Cloudflare’s global network, and between roughly 7:20 and 11:30 AM EST engineers had to roll everything back and restart systems. Cloudflare says this wasn’t an attack; it was an unfortunately spectacular internal software error. They’ve apologized and promised fixes. We’re sorry too — for the downtime and the disruption to your day.
If you’re wondering why we—and most small businesses—put so much of our infrastructure behind a single vendor like Cloudflare, the short answer is: because there really isn’t a practical alternative. Cloudflare bundles CDN, global edge points, DDoS protection, WAF, DNS, TLS termination, bot management, and performance routing into a single, battle-tested service that works at a scale and price point small teams can actually afford. Building or operating an equivalent global edge network on your own? That’s not a “let’s try it this weekend” problem. Running multiple providers to avoid a single point of failure (multi-CDN/multi-WAF) is possible — but it’s expensive, operationally complex, and introduces its own new failure modes. For teams of one or five, the cost and coordination overhead often outweigh the theoretical benefit.
We want to be blunt: outages like this are fundamentally a reminder of how tightly coupled modern web infrastructure is. A single misbehaving configuration at one provider can cascade into a global outage that affects unrelated services across the web. As much as we’d love to wave a magic wand and make us immune, the reality is that most of the tools that protect, speed up, and secure our sites are centralized in a handful of providers. That concentration buys you affordability, performance, and security — and also concentrates risk.
That said, we’re not helpless. We’ve taken the outage seriously and are doing what we can on our side: strengthening caching and graceful degradation so essential features stay online longer during upstream problems, improving monitoring and alerting so we can flip to safe modes faster, and improving customer communications so you know what’s happening without refreshing status pages every five seconds. Some mitigations (like a true multi-CDN setup) are costly and imperfect; others (better fallbacks, clearer error messaging) are practical and helpful. We’re doing both. Again: we’re sorry for the interruption. Cloudflare has called the downtime “unacceptable” and is working on fixes to prevent configuration-driven failures like this. We’re keeping a close eye on their post-mortem and re-evaluating our own resilience plans with realism — not hype. If you have questions, need help with a workflow that was interrupted, or want a plain-English rundown of what we’ve changed on our end, reach out — we’ll get back to you without the BS. Your business, your data — simple as that.
