Yes, @Mor Levi , I wrote a post about it and you can read it here.
Let me know if this helps.
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Hi,
I'm trying to setup a couple of alerts on SQL Server which sends me a message when the alert executes. I've setup an account in Database Mail, which sends an email via "smtp.office365.com", using port 587. Below is the settings I used (I removed the domain of the accounts for security purposes):
When I to send a test message, I get the following errors, depending on whether I have the "This server requires a secure connection" checkbox checked.
If this checkbox is not checked, I get:
Exception message: cannot send mails to mail. The server response was 5.7.3 STARTTLS is required to send mail
If this checkbox is checked, I get:
The server response was 5.7.57 Client not authenticated to send mail.
I also tried port 25, basic and anonymous authentication and a variety of users when using basic authentication, but the same errors appear. I was wondering how do I set the account up so I could send a message from SQL Server?
Sincerely,
Jason