The key thing to understand is who is doing the checking and from where. The authority is validating from its own servers, on the public internet, not from your machine. So "it works in my browser" tells you very little — your browser may be inside the network, cached, or using a different address.
What happens in an HTTP challenge:
- The client asks for a certificate and receives a token.
- It writes the token to a file under
/.well-known/acme-challenge/on your site. - The authority requests that exact URL over plain HTTP on port 80, from several locations.
- It must receive the token, with no redirect to somewhere it cannot follow and no authentication in the way.
So the diagnostic is to fetch that URL yourself the way the authority does — from outside your network, over HTTP, following redirects, and watch what comes back. That single test identifies the failure in nearly every case.