This morning started like any other. Coffee. Kids. Email. Calendar check. Calendar check… calendar, what the…?
My Skylight calendar wouldn’t load. I assumed it was my Wi-Fi. Then maybe the OS. Then maybe the device. Eventually, after my tech troubleshooting ritual proved fruitless, the real culprit appeared in my newsfeed.
A widespread Cloudflare outage impacting hundreds of digital services across the globe.
Cloudflare quickly acknowledged an “internal server error on Cloudflare’s network,” confirming that the issue was not isolated to Skylight users like me, but rather part of a massive multi-platform disruption.
This serves as another reminder to all of us just how much of the internet quietly runs on shared infrastructure behind the scenes.
As a marketer and a family man, I’m looking at both sides of this situation. In moments like these, two things matter: understanding the technology that failed, and communicating effectively with the people impacted by it. Let’s unpack both.
What is Cloudflare, and what does it actually do?
Cloudflare is one of the invisible engines powering the modern internet. It’s a massive global network that sits between websites and the people who access them. More technically, Cloudflare acts as a reverse proxy, routing all incoming user traffic through Cloudflare’s servers before delivering it to a website’s origin server.
This setup enables several essential functions:
Faster websites: Cloudflare makes websites load quickly by keeping copies of them in lots of places around the world. That way, when you click a site, you get it from the spot closest to you.
Improved safety: Cloudflare protects websites from hackers and bad actors on the internet. It stops huge waves of fake traffic, blocks harmful robots, and keeps out common attacks.
More reliable: If huge numbers of people try to visit a website at the same time, Cloudflare helps it stay online. It spreads all the visitors across many computers so the website doesn’t get overwhelmed.
Safer connections: Cloudflare helps make sure the connection between your computer and a website is locked and secure, using special digital codes and encryption.
Smarter computing: Cloudflare lets companies run small bits of code on computers all around the world, instead of only one place, helping apps work better and run smoother.
Because so many brands use Cloudflare for one or more of these services, a failure in its network doesn’t just affect one website. It affects the entire infrastructure behind many websites.
The scope of today’s Cloudflare outage
Reports confirmed that major platforms were impacted, including:
- X (formerly Twitter), which saw widespread downtime as the outage unfolded
- ChatGPT / OpenAI, whose services degraded significantly during the incident
- Shopify, leading to eCommerce interruptions for countless merchants
- Dropbox
- Coinbase
- League of Legends
- Moody’s
- NJ Transit, whose app and website experienced outages affecting commuters
And according to broader reporting, additional platforms such as Spotify, Canva, Quora, Discord, IKEA, and Perplexity AI were also disrupted during the event.
And let’s not forget about that Skylight calendar.
Cloudflare indicated it was actively deploying fixes and restoring service, though elevated error rates continued for some users. As is often the case with distributed infrastructure, full recovery takes time.
Why this matters for brands
When a company like Cloudflare encounters a major failure, the consequences spill far beyond a single outage window. Brands may face:
- Customer frustration
- Delayed transactions
- Interrupted support channels
- Downed log-ins or inaccessible dashboards
- Issues with ad delivery and attribution
- Drops in eCommerce conversion rates
- Impacts on mobile app functionality
Even if your website isn’t directly on Cloudflare, your digital ecosystem might still be impacted. Social networks, CRMs, analytics platforms, booking providers, API connections, or identity services can all depend on it.
For Envisionit, none of our client websites rely on the failing portions of the Cloudflare ecosystem. All the sites we host remained online and functional throughout the incident.
However, many social platforms, ad destinations, and third-party systems used in paid media programs were impacted. That changes how we communicate with our customers and what we advise them to monitor.
Pause paid media campaigns during Cloudflare outages
When an outage affects site accessibility, the best thing to do is to pause all paid media campaigns driving traffic to your site. If users can’t load your pages, or experience broken sessions, you’re basically paying for clicks that can’t convert.
Outages can also disrupt analytics. Tracking scripts can fail to fire, conversions might not record, and attribution can break, which creates gaps that make future optimization a lot harder.
And if a disruption is prolonged, both paid and organic channels feel the effects.
We immediately paused our clients’ affected campaigns, keeping them informed as we acted in their best interest and inviting them to contact us with any questions or concerns.
Across all channels, the priority should be to protect user experience, safeguard performance data, and get your campaigns back up once everything has been restored.
The critical role of communication during outages
Technology fails. Systems fail. Even the internet’s most reliable players fail.
But brand trust doesn’t have to fail with it.
When something breaks (especially when it’s something outside your control) the speed, clarity, and empathy of your communication become the most important tools you have.
Here’s what brands should consider when developing communication and responses for moments like these:
1.) Communicate early and with empathy
Even if you don’t yet know the full cause, it’s better to acknowledge the disruption early. People want reassurance that you’re aware, alert, and actively monitoring the issue.
An empathetic message signals:
- We see what you’re experiencing
- We understand the inconvenience
- We won’t leave you guessing
2.) Explain the issue so it’s easy to understand
You don’t need to dig into routing anomalies or DNS propagation paths. Just explain what you know in terms that your audience will understand and appreciate.
- What happened (e.g., a major outage at a global infrastructure provider)
- How it may affect users (i.e., delays, errors, or feature unavailability)
- What you’re doing (i.e., monitoring, validating, preparing contingencies)
Skylight, for example, loaded a prewritten chatbot message acknowledging its reliance on Cloudflare and explaining why users were experiencing issues. This was a small but thoughtful touch that reduced my anxiety a bit, by letting me know that this wasn’t an issue I could fix on my end.
3.) Use multiple communication channels
During an outage, assume nothing is fully reliable. Spread the message across:
- Website banners or notifications
- Chatbot or live chat
- Social media posts
- Email or SMS alerts
- Status pages
- In-app messages
If one channel fails, others remain available.
4.) Provide clear points of contact
Tell customers where to go and who to talk to if they need help. Direct lines of communication reduce the risk of misinformation and reinforce trust.
Internally, give your customer-facing teams talking points and a short FAQ so messaging stays consistent.
5.) Maintain transparency without over-promising
Avoid guesses. Avoid timelines you don’t control. Instead, share:
- What is known
- What is being investigated
- What you will update when you know more
Trust grows when communication remains steady and grounded in truth.
6.) Follow up after the outage
Once systems stabilize, send a clear wrap-up communication
- What happened
- How it was resolved
- What safeguards will be put in place
- What lessons were learned
Customers appreciate being kept in the loop not just during the crisis, but after the dust settles.
How Envisionit is supporting clients today
While none of our hosted websites were impacted, many of the platforms our clients use were affected. We’ve been actively:
- Monitoring platform performance
- Identifying potential disruptions to ad delivery
- Alerting clients whose campaigns may experience short-term anomalies
- Preparing contingency options if needed
Outages happen, trust is built in the response
Cloudflare has gone down before, and it will most likely experience issues in the future that will disrupt business. And if it’s not Cloudflare, it might be Crowdstrike, or Microsoft Azure, any of the other silent systems we depend upon. It’s a good idea to have a strategy in place to address these issues when they arrive instead of scrambling to put something together.
Think about the dad sitting at his kitchen table, wondering why his digital calendar won’t work (or, you know… perhaps consider a customer situation more specific to your business offering). Think about how your customers’ lives are impacted, where they might turn for help, and what they would need to know.
In these moments of disruption, brands can build trust by communicating proactively and with empathy.
