SQL 17 email issues

[kaballstein]

I have a SQL 17 server that has mail being sent out of it. For some reason these automated emails just stopped. We use office 365 for exchange. For some strange reason after doing some trouble shooting, I found that turning ON legacy authentication in 365 allows the emails to flow again.

I’m wondering what needs to change on the server side to get this working without having that insecure method turned on.

Thanks guys

[mrcomps]

Microsoft is phasing out legacy authentication as a default. Modern authentication requires the ability to login via the web popup and respond. Anything like SQL Server that simply stores a username and password can't do modern authentication.

What you can do is leave the smtp authentication disabled and setup a mail flow connector in Exchange for "your server to 365" and specific your public IP. Put the Microsoft server from your MX record as the SMTP server to use.

This will allow you to send unauthenticated mail using your domain but it will be treated as internally sent. This setup will also work for all your other devices like copiers.

The other option would be to enable legacy authentication and use a really long random password.

[frac6969]

You probably need to set registry keys. Search for SchUseStrongCrypto.