Cloudflare is making headlines for surprising customers with a massive bill, and only giving them 24 hours to pay for an entire year.

SysOps engineer Robin Dev took to Substack to detail the issues his company experienced when Cloudflare reached out to try to migrate the account to its Enterprise plan:

TL;DR:

We’ve been on the Cloudflare Business plan ($250/month) for years. They suddenly contacted us and asked us to either pay them $120k up front for one year of Enterprise within 24 hours or they would take down all of our domains. While this escalated up our business we had 3 sales calls with them, trying to figure out what was happening and how to reach a reasonable contract in a week. When we told them we were also in talks with Fastly, they suddenly “purged” all our domains, causing huge downtime in our core business, sleepless nights migrating away from CF, irreparable loss in customer trust and weeks of ongoing downtime in our internal systems.

Throughout the process, Cloudflare sent emails to Dev’s company that conflicted with the action Cloudflare was taking. For example, some emails seemed to indicate a monthly plan was possible, even though Cloudflare was demanding an entire year’s payment upfront. Similarly, Cloudflare sent an email when it suspended the company’s account saying “this account suspension does not impact, disable, or remove your current services.” In reality, nothing could be further from the truth.

Cloudflare had suddenly deleted all of our domains. All of our DNS records, caching setup, rate limits, whitelists, gone. Our public website, our incoming emails (including support emails from our customers) and our internal infrastructure, our authentication configuration on Cloudflare Access, down.

The email says “this […] does not impact current services”, so we frantically wrote them a support ticket but got no response. So we called in our SysOps team and started migrating our main site to Fastly. We had the basics after a few hours, but even then, a “NS” DNS entry change apparently takes a pretty arbitrary time to propagate everywhere, from 1h to 48 hours. We’re still recovering from the aftermath.

As Dev points out, much of the issue comes from Cloudflare’s opaque terms, making it almost impossible to predict if or when Cloudflare will take such action.

Cloudflare has absolutely no information on when they will force you into custom billing, but when they start “urgently” needing to talk to you you’re probably not going to get out until you have a juicy custom contract with them. There’s a reason why they have no public information anywhere on traffic limits or Enterprise pricing. Their Sales team will use anything (like having multiple domains) as fuel to force your whole account to Enterprise , no matter if it is fixable in a simple way.

Popular YouTube and developer ThePrimeagen theorizes that Cloudflare’s sales team is engaging in this behavior in part because the company’s CEO called out the sales team for under-performing.

Although we’ve won a third of the Fortune 500 customers, if we’re honest with ourselves, we saw a lot of our success with our enterprise customers because our products were so good and solved real problems that every big company faces. That allowed many on our sales team to succeed largely by just taking orders. When the fish are jumping right in the boat, you don’t need to be a very good fisherman. But at the risk of mixing watering metaphors, as the tide goes out, you get a clear view who’s not wearing shorts.

The macroeconomic environment has gotten harder, and we’re seeing that some on our team aren’t dressed for work. Digging in with Marc, we’ve identified more than 100 people on our sales team who have consistently missed expectations. Simply put, a significant percentage of our sales force has been repeatedly underperforming based on measurable performance targets and critical KPIs. That’s obviously a problem.

As a result, the sales team may be engaging in actions that can only be described as shakedowns in an effort to save their jobs.