Matthew Prince

Chief Executive Officer and Co-Founder, Cloudflare - Leading post-incident response and policy discussions

On February 16, 2026, a single misconfigured routing update at Cloudflare's Ashburn, Virginia data center cascaded across the internet, taking down X for three hours, degrading Amazon Web Services' largest region, and disrupting thousands of websites globally. The error took 40 minutes to identify but four hours to fully resolve because corrupted routing tables had already spread to upstream providers worldwide.

Updated Feb 16

Co-founder and CEO, Cloudflare - Publicly accountable for repeated outages through early 2026 and ongoing reliability reforms

From November 2025 through February 2026, Cloudflare suffered multiple major global outages, including a three-hour disruption on November 18, 2025, a 25–30 minute WAF misconfiguration incident on December 5, 2025, a BGP routing failure on January 22, 2026, and edge network instability on February 4, 2026. These events temporarily took down services like LinkedIn, Zoom, Shopify, Coinbase, ChatGPT, X, Spotify, and others that rely on Cloudflare’s edge network, content delivery, and security services, affecting an estimated significant portion of global HTTP traffic during peaks.

Updated Feb 5

Co-Founder & CEO, Cloudflare - Leading Cloudflare's AI economy strategy

For two years, AI companies have trained their models on web content while paying for almost none of it. That era may be ending. Cloudflare's acquisition of Human Native, announced January 15, 2026, adds a London-based data marketplace to an infrastructure stack that already includes bot-blocking tools, pay-per-crawl billing, and the x402 machine payment protocol built with Coinbase. Days after the acquisition, Cloudflare signaled its next move: a dollar-backed stablecoin called NET to power AI micropayments, turning the x402 protocol from concept into usable financial infrastructure.

Updated Jan 16