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The problem is .well-known has to be accessible via http. # curl "http://borbach.com/.well-known/acme-challenge/ysITPUa8hTIqNhE7FjrKF9WjF0QDi4AUgdjhK5ioL3U" <html> <head><title>301 Moved Permanently</title></head> <body> <center><h1>301 Moved Permanently</h1></center> <hr><center>nginx</center> </body> </html> As you can see requests for http get redirected to https so SSL verification will always fail. I disabled redirection to https and now it returns the contents of the verification file instead of redirecting to https. # curl "http://borbach.com/.well-known/acme-challenge/ysITPUa8hTIqNhE7FjrKF9WjF0QDi4AUgdjhK5ioL3U" ysITPUa8hTIqNhE7FjrKF9WjF0QDi4AUgdjhK5ioL3U.JYseh45lQBxj41K6qwq7KQASWpf6M7NBo1lNHke015E Here is the recommended way to redirect to https, while making an exception for .well-known to be accessed via http RewriteEngine On RewriteCond %{HTTPS} !=on RewriteCond %{THE_REQUEST} !/.well-known/(.*)$ [NC] RewriteRule ^ https://%{HTTP_HOST}%{REQUEST_URI} [L,R=301] I added the above code to your .htaccess and I reissued Let's Encrypt via Plesk for you and now everything is working as expected. https://www.sslshopper.com/ssl-checker.html#hostname=borbach.com1 point