Resolution

Summary: When sending a test email, you may get the following error:

The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM [AM0PR06CA0080.eurprd06.prod.outlook.com]

This article contains step-by-step instructions on how to resolve this issue.

Applies to: Cayosoft Administrator 7.3.0 or later

Resolution

1. Check that the account that is used in the Cayosoft Administrator console under Configuration > Settings > Email Settings (SMTP) has an Exchange Online license.
2. Check that the account password is set correctly.
3. Check that you can send and receive an email through Outlook.

4. Run the PowerShell script below to test if the issue is related to your environment or if this is a Cayosoft Administrator Service issue. When prompted, specify Microsoft 365 Administrator credentials:

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     $cred = get-credential                       Send-MailMessage –From <administrator@yourdomain.com> –To <administrator@yourdomain.com> –Subject “Test Email” –Body “Test Text” -SmtpServer smtp.office365.com -Credential $cred -UseSsl -Port 587          

5. If you still get the error " The SMTP server requires a secure connection or the client was not authenticated " run the script below to enable authenticated SMTP for the Microsoft 365 administrator mailbox: 

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    Set-CASMailbox <administrator@yourdomain.com> -SmtpClientAuthenticationDisabled $false 

6. Wait for about an hour. 
7. Check that now test emails can be sent.