If you move canadawebservice.example
to Cloudflare, keep the DNS record for “server1971
” (equal to the fully-qualified domain name “server1971.canadawebservice.example
”) set to Unproxied (
) / DNS-only.
That could be Outlook, - some email clients will try typical mail server names, such as e.g. mail.steveswebsite.example
, imap.steveswebsite.example
, pop.steveswebsite.example
, pop3.steveswebsite.example
, and so forth, if it is unable to determine it’s configuration automatically.
Outlook may therefore be stopping at mail.steveswebsite.example
, because it sees that this specific server name works fine.
If you move steveswebsite.example
to Cloudflare, keep the DNS record for “mail
” (equal to the fully-qualified domain name “mail.steveswebsite.example
”) set to Unproxied (
) / DNS-only.
I would recommend you to use a server name on the hosting provider’s domain name, and not one on each individual customer’s domain name.
Pointing all your customers towards something like “server1971.canadawebservice.example
”, or “imap.canadawebservice.example
” would mean that you would be able to change the IP address(es) for the given host name, when using one of your own organisation’s domain names.
You wouldn’t always have that operational benefit when using the individual customer’s domain name, such as e.g. “mail.steveswebsite.example
”, which would mean that some customers, such as e.g. Steve, would get mad at you, when you perform changes to your infrastructure.
The best practice is to use the hosting provider’s domain name, for accessing services operated by that hosting provider.
If your customer is onboarding their domain to Google Workspace, they would be using imap.gmail.com
for IMAP, or smtp.gmail.com
for SMTP traffic.
If your customer is onboarding their domain to Microsoft’s Office 365, they would similarily be using outlook.office365.com
for IMAP, or smtp.office365.com
for SMTP traffic.


If “mail.steveswebsite.example
” was to be used for Google Workspace or Microsoft Office 365, Steve would be seeing a certificate alert when connecting, because neither of those organisations would be able to maintain an individual certificate for each customer’s own domain name, on their servers, that easily.
They can however maintain encryption certificates easily, when the DNS name being used is below one of their own domain names.
Can you share that exact error?
Perhaps a screenshot?
I’m wondering if you’re maybe misinterpreting the error, as being a SMTP error, while in theory, it may be a certificate error, similarly to the example mentioned above?
That said, -
Note: In my response, you will see that I have changed your domains to be on the “.EXAMPLE
” TLD, rather than the “.CA
” or “.COM
” you used, as these domains you mentioned already exist, and sound to be held by someone else.
Domains like e.g. example.com
, example.net
and example.org
are standardized as example domains, such as for use in e.g. documentation, and, like in your case if you are not actually sharing a real domain name.
If you need another TLD to use in examples, arbitrary domains can be shared under “.test
”, “.example
”, “.invalid
”, and/or “.localhost
”.