THANK YOU, this fixed it. My site email address was blank. Im in favor of making that a required field with a default (e.g. noreply@drupal.site), but maybe because that is because I just got burned! :)

Thanks again, Chris

What happens if you change the Drupal site email address to the same

From address that one the successful test emails you sent used? Or

change your previously successful test emails to come from your Drupal site address?

I suspect that your Drupal site address isn't allowed to relay through your MTA/smarthost.