Office 365 Database Emails with SSMS 2019

Mucho85 1 Reputation point

I have SSMS 2019 set up with an Office 365 account, which has its own full mailbox. The settings are shown in the screenshot, with the email address and username being the full email address.


When I use the inbuilt Send Test E-Mail function, the mail fails to send and I get the following error.

The mail could not be sent to the recipients because of the mail server failure. (Sending Mail using Account 1 (2021-03-15T17:20:25). Exception Message: Cannot send mails to mail server. (The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.57 Client not authenticated to send mail. [XXXXXXXXXXXXX.XXXXXXX.PROD.OUTLOOK.COM]).

SSMS is installed on a Windows Server 2019 VM in Azure, and is not joined to Azure AD. Does anyone have any ideas on what the issue may be?

I am also unable to send email through SQL Server Reporting Services

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A family of Microsoft relational database management and analysis systems for e-commerce, line-of-business, and data warehousing solutions.
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  1. Olaf Helper 43,161 Reputation points

    Seems your email configuration is correct.
    See How to set up a multifunction device or application to send email using Microsoft 365 or Office 365 for a step-by-step guide.

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  2. Borcard François 1 Reputation point


    I have the same problem. Any help would be appreciated

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