If you sending the email through the same server, make sure it is configured to use mail.thegravelguy.ca (assuming that points to the IP address of your server) as the server name and not thegravelguy.ca as that is now proxied through a Cloudflare IP address. https://cf.sjr.dev/tools/check?13f65efd7ec841d983ecc83e12e10087#dns-mail
If your server sends email you will also want to add its IP address to your SPF rule as a will be the Cloudflare proxy IP address again and not your mail server’s IP address.
I can’t be sure as I can’t see the configuration, but likely previously your mail software pointed at the IP address of your server using your domain name.
Now you are using Cloudflare the public IP address of your server is a Cloudflare one, so your mail server cannot be reached that way. Instead, configuring your mail to use mail.thegravelguy.ca points to a DNS record that is not proxied and I guess points at your server.
@sjr I guess I needed to walk away from the screen and rethink this, and low and behold, I was able to solve the mystery!!
I had inadvertently selected TLS instead of SSL, and had the SMTP Server name with a slight error. It should have been mail.thegravelguy.ca instead of just thegravelguy.ca, and I made the switch to SSL…and voila!
Test email went through!
I have placed the A record for ‘mail’ in the DNS to DNS Only.