To everyone saying that Caddy made it simple for automated LE; I agree, but also, it's not that difficult to setup with NGINX: Edit /var/nginx/ssl_common.conf

To everyone saying that Caddy made it simple for automated LE; I agree, but also, it's not that difficult to setup with NGINX: Edit /var/nginx/ssl_common.conf ssl_certificate /etc/letsencrypt/live/<site>/fullchain.pem; ssl_certificate_key /etc/letsencrypt/live/<site>/privkey.pem; location ^~ /.well-known/acme-challenge/ { default_type "text/plain"; allow all; root /var/www/example; auth_basic off; } Edit crontab, add: 30 2 * * 1 /bin/certbot -a webroot --webroot-path=/var/www/example renew --renew-hook "systemctl restart nginx" Make the cert mkdir -p /var/www/example certbot certonly --webroot -w /var/www/example/ -d www.example.com In your NGINX HTTPS server blocks add: include ssl_common.conf That should be it...