Dry run failure

contents of /etc/apache2/sites-enabled/maillist.naturalintelligence.us.conf
‘’’
<VirtualHost :80>
ServerName maillist.naturalintelligence.us
Redirect permanent / https://maillist.naturalintelligence.us/
RewriteEngine on
RewriteCond %{SERVER_NAME} =maillist.naturalintelligence.us
RewriteRule ^ https://%{SERVER_NAME}%{REQUEST_URI} [END,NE,R=permanent]
DocumentRoot /var/www/html/maillist.naturalintelligence.us/public_html
ErrorLog /var/www/html/maillist.naturalintelligence.us/logs/maillist.naturalintelligence.us-error.log
CustomLog /var/www/html/maillist.naturalintelligence.us/logs/maillist.naturalintelligence.us-access.log combined
Options ExecCGI
AddHandler cgi-script .pl

Options +ExecCGI
FcgidConnectTimeout 20
AddType application/x-httpd-php .php
AddHandler application/x-httpd-php .php
Alias /php7-fcgi /usr/lib/cgi-bin/php7-fcgi
ProxyPassMatch " ^/(.
.php(/.*)?)$" “unix:listen = /var/run/php/php7.3-fpm_example.com.sock|fcgi://localhost/var/www/html/example.com/public_html/”


‘’’

contents of /etc/apache2/sites-enabled/maillist.naturalintelligence.us-le-ssl.conf
‘’’

<VirtualHost :443>
ServerName maillist.naturalintelligence.us
Redirect permanent / https://maillist.naturalintelligence.us/
DocumentRoot /var/www/html/maillist.naturalintelligence.us/public_html
ErrorLog /var/www/html/maillist.naturalintelligence.us/logs/maillist.naturalintelligence.us-error.log
CustomLog /var/www/html/maillist.naturalintelligence.us/logs/maillist.naturalintelligence.us-access.log combined
Options ExecCGI
AddHandler cgi-script .pl

Options +ExecCGI
FcgidConnectTimeout 20
AddType application/x-httpd-php .php
AddHandler application/x-httpd-php .php
Alias /php7-fcgi /usr/lib/cgi-bin/php7-fcgi
ProxyPassMatch " ^/(.
.php(/.*)?)$" “unix:listen = /var/run/php/php7.3-fpm_example.com.sock|fcgi://localhost/var/www/html/example.com/public_html/”

SSLCertificateFile /etc/letsencrypt/live/maillist.naturalintelligence.us/fullchain.pem
SSLCertificateKeyFile /etc/letsencrypt/live/maillist.naturalintelligence.us/privkey.pem
Include /etc/letsencrypt/options-ssl-apache.conf


‘’’

Are you using .htaccess files or anything like wordpress?

No .htaccess or any other CMS. I am using Sympa however which has a web interface that uses apache.

Well there is a problem in there… somewhere:
The HTTP forwards to HTTPS (as expected):

 curl -Iki http://maillist.naturalintelligence.us/
HTTP/1.1 301 Moved Permanently
Date: Tue, 25 Aug 2020 00:38:19 GMT
Server: Apache/2.4.38 (Debian)
Strict-Transport-Security: max-age=63072000; includeSubDomains; preload
X-Frame-Options: SAMEORIGIN
X-Content-Type-Options: nosniff
Location: https://maillist.naturalintelligence.us/
Content-Type: text/html; charset=iso-8859-1

But the HTTPS also redirects to HTTPS (endless loop):

curl -Iki https://maillist.naturalintelligence.us/
HTTP/1.1 301 Moved Permanently
Date: Tue, 25 Aug 2020 00:38:34 GMT
Server: Apache/2.4.38 (Debian)
Strict-Transport-Security: max-age=63072000; includeSubDomains; preload
X-Frame-Options: SAMEORIGIN
X-Content-Type-Options: nosniff
Location: https://maillist.naturalintelligence.us/
Content-Type: text/html; charset=iso-8859-1

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