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Is it at all achievable to be fronted by a CDN but fallback to the raw server in case the front falls off? Better to be vulnerable to DDoS than be unreachable altogether

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With CloudFlare specifically probably not. IIRC, they require DNS resolution of your domain to operate so if they’re down, I don’t see how you’d change it to route directly to the underlying site.

Even if you could, having two sets of TLS termination is going to be a pain as well.

But then you end up potentially exposing the origin server. This could be an opt-in option though

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