Please fill out the fields below so we can help you better. Note: you must provide your domain name to get help. Domain names for issued certificates are all made public in Certificate Transparency logs (e.g. crt.sh | example.com), so withholding your domain name here does not increase secrecy, but only makes it harder for us to provide help.
The operating system my web server runs on is (include version): Mac High Sierra
My hosting provider, if applicable, is: network solutions
I can login to a root shell on my machine (yes or no, or I don't know): Yes
I'm using a control panel to manage my site (no, or provide the name and version of the control panel): No
The version of my client is (e.g. output of certbot --version or certbot-auto --version if you're using Certbot): Certbot Not Supported-Created the certificate using latest Certbot on a Mac Monterey machine
I have loaded the certificate into my keychain. It is trusted. When I assign the certificate to the website using Server App, the certificate is not considered SSL.
The following renewal configurations were invalid:
/etc/letsencrypt/renewal/www.classicautoserv.com.conf
sudo apachectl -t -D DUMP_VHOSTS
AH00526: Syntax error on line 152 of /private/etc/apache2/extra/httpd-ssl.conf:
SSLCertificateKeyFile: file '/etc/letsencrypt/live/hprauto.com/privkey.pem' does not exist or is empty
That looks like you might have tried to copy some files around and overwrote it.
One should never need to copy any files into the /etc/letsencrypt/ path.
This also points towards a copy gone bad and overwrote a key file.
At this point I can't be sure of what is the best way out of this mess.
One path might be to remove the entire /etc/letsencrypt/ path and reissue your LE certs.
But you would have to review all your steps / scripts to ensure you won't be making this same mistake.