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It occurs after hitting "send" on the Apple Mail app for the first email each and every time after I restart the computer.
I have 5 email addresses, only one of these is through your server, I get the message without regard to which email address (@iCloud.com, @GMail.com, etc.) is the first to send the email.
The error message pops up a minute or so after hitting the send button.
The email is not sent, but rather it is stuck in the out basket. No emails can be sent until the problem is fixed.
The email can be in limbo for hours if I step away from the computer.
If I hit Continue, that and every subsequent email is sent normally.
But, if I do not see the error, all email activity is stopped.
This leads to frequent "But I sent you the email hours ago" statements, when the email is still in limbo and I have not noticed the problem.
This has been driving me crazy for almost 40 months!
The SMTP is that which you provide me.
It thinks there is a problem with the certificate for the site that I am paying you for and you are providing me.
When I click on the Certificate button, I get
What must you do to the certificate to resolve this?