At Sentry, we’re obsessed with things not breaking. It’s kind of our whole deal. But for a while, our own marketing site was testing that obsession.
Much of what you see on sentry.io (the marketing site, blog, open source microsite, etc.) were running on a fleet of legacy Gatsby sites powered by a traditional headless CMS. On paper, it worked. In practice, we were juggling a fragile web of plugins, restrictive schemas, and external API dependencies that loved to fail right when we needed to ship.
So, we did what any sane engineering team would do: we ripped it out and replaced it with Astro, Markdown, and AI-driven automation.
The problem: the “headless” headache
Our old stack was starting to feel like a Rube Goldberg machine.














