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
- Check that account that is used in Home > Configuration > Settings > Email Settings (SMTP) has Exchange Online license
- Check that the account password is set correctly.
Check that using this account you can send and get an email through Outlook.
- Run the PowerShell script below to test if the issue is related to your environment or if this is CayoAdmin Service issue. When prompted specify Office 365 Administrator credentials:
$cred = get-credential Send-MailMessage –From <firstname.lastname@example.org> –To <email@example.com> –Subject “Test Email” –Body “Test Text” -SmtpServer smtp.office365.com -Credential $cred -UseSsl -Port 587
- 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 Office 365 administrator mailbox:
Set-CASMailbox <firstname.lastname@example.org> -SmtpClientAuthenticationDisabled $false
- Wait for about an hour.
- Check that now test email can be sent.
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