Thomas Sobolik discusses the challenges of monitoring static web applications and provides best practices for effective monitoring. Static sites are currently a popular solution for many lightweight web applications, such as corpsites, blogs, job listings, and documentation repositories. With the majority of backend logic migrated to the build process and CI/CD, reliance on CDNs for delivering both static assets and page markup, and limited options for instrumenting the frontend to track UX performance, monitoring the health and performance of static web apps presents some challenges. The author suggests collecting real user session data as well as performance and security data from the CDN provider to optimize caching and delivery. They also recommend monitoring the build-to-deploy cycle, including the supplemental build infrastructure, CI pipelines, and synthetic tests. Additionally, they suggest collecting frontend session data to track page loads and their dependent CDN requests, CDN request logs, as well as health, performance, and security data from the CDN provider. The author emphasizes the importance of tracking bandwidth usage for visibility into CDN cost, security monitoring data from the CDN, and maintaining healthy testing to avoid deploying regressions. Finally, they recommend using a comprehensive solution like Datadog to monitor each layer of the static web stack in a unified platform.