Troubleshooting SMTP Server settings

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 account that is used in Home > Configuration > Settings > Email Settings (SMTP) has Exchange Online license.

2. Check that the account password is set correctly.

3. Check that using this account you can send and get an email through Outlook.

4. Run the PowerShell script below to test if the issue is related to your environment or if this is the 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 SMTP server requires a secure connection or the client was not authenticated error run the script below to enable authenticated SMTP for 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 email can be sent.