A Good: All checks /.well-known/acme-challenge/random-filename without redirects answer with
the expected http status 404 - Not Found. Creating a Letsencrypt certificate via http-01 challenge
should work. If it doesn't work: Check your vHost configuration (apachectl -S, httpd -S, nginx -T).
Every combination of port and ServerName / ServerAlias (Apache) or Server (Nginx) must be
unique. Merge duplicated entries in one vHost. If you use an IIS, extensionless files must be
allowed in the /.well-known/acme-challenge subdirectory. Create a web.config in that directory.
Content: <configuration><system.webServer><staticContent><mimeMap fileExtension="." mimeType="text/plain" /></staticContent></system.webServer></configuration>.
If you have a redirect http ⇒ https, that's ok, Letsencrypt follows such redirects to port 80 / 443
(same or other server). There must be a certificate. But the certificate may be expired, self
signed or with a not matching domain name. Checking the validation file Letsencrypt ignores
such certificate errors.