Cloudflare's network complexity, driven by rapid expansion of services like Bot Management, Workers, and Zero Trust, has repeatedly led to self-inflicted critical incidents from internal configuration changes rather than external attacks. Multiple outages occurred in 2025, including a major June disruption to core services, a November 18 event triggered by database permission updates that ballooned feature files, and a shorter December 5 incident tied to security patch deployments. These patterns, detailed in company postmortems, highlight risks in large-scale propagation and change management. Trader sentiment reflects this track record of frequent red-level issues, alongside the company's scale as a key internet infrastructure provider, with resolution hinging on any new critical classification by the deadline. No major scheduled events alter the baseline risk profile.