Error messages with email setup in my Business software

[yardsentry]

I have software that allows me to email estimates statements bills etc. Using Gmail is flawless. When I try to use Outlook Office365 or GoDaddy workspace all I get is "Timeout" or "The SMTP server requires a secure connection or the client was not authenticated. the server response was: 5.7.57; Clent was not authenticated to send anonymous mail during MAIL FROM [MN2PR20CA0009.namprd20.prod.outlook.com]"

[davisdre317 · Accepted solution]

@yardsentry

Hello and thank you for reaching out to the GoDaddy community.

You might need to set it up for direct send. For direct send, use the MX endpoint for your Office 365 tenant, which ends with "mail.protection.outlook.com."