@KevinTheJedi I am running Debian 12. sudo a2enmod rewrite returns Module rewrite already enabled
I made the suggested changes and rebooted server. Still no luck. 🙁 note the 'Not Found' error message comes up after I enter the credentials (see screenshot below).

see new file config as per your recommendation:
`<VirtualHost *:80>
RewriteEngine on
RewriteCond %{SERVER_NAME} =support.example.com
RewriteRule ^ https://%{SERVER_NAME}%{REQUEST_URI} [END,NE,R=permanent]
ServerAdmin webmaster@localhost
DocumentRoot /var/www/html
<Directory /var/www/html/helpdesk>
Options Indexes FollowSymLinks
AllowOverride All
Require all granted
</Directory>
ErrorLog ${APACHE_LOG_DIR}/error.log
CustomLog ${APACHE_LOG_DIR}/access.log combined
</VirtualHost>`