Powershell – Sending mail notifications from Windows Server 2003 Powershell 2.0 to Office 365

emailmicrosoft-office-365powershellwindows-server-2003

My script is meant to suck up errors in scheduled tasks that don't complete correctly and sends them to my email address via Office365:

$reportHTML = Get-Content C:\windows\tasks\SchedLgU.Txt | Select-String -Pattern "an exit code of \(1\)" -context 2
$reportHTML = Out-String -InputObject $reportHTML

#TODO Add an if statement

$emailUsername = "myemail@somedomain.com"

#TODO: Change this to a file....
#$emailPassword = cat "C:\ps\emailCred.txt" | convertto-securestring
$emailPassword = ConvertTo-SecureString "somepassword" -AsPlainText -Force


$emailCred = new-object -typename System.Management.Automation.PSCredential($emailUsername, $emailPassword)



Send-MailMessage -To "myemail@somedomain.com"  -Body $reportHTML -Subject 'Job(s) Failed' -UseSsl -SmtpServer 'smtp.office365.com' -From 'myemail@somedomain.com' -Credential $emailCred

But when I run it, I get the following error message:

Send-MailMessage : The SMTP server requires a secure connection or the client was not authenticated. The server respons
e was: 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM
At C:\ps\FailedJobNotificiation.ps1:14 char:17
+ Send-MailMessage <<<<  -To "myemail@somedomain.com"  -Body $reportHTML -Subject 'Job(s) Failed' -UseSsl -SmtpServ
er 'smtp.office365.com' -From 'myemail@somedomain.com' -Credential $emailCred
    + CategoryInfo          : InvalidOperation: (System.Net.Mail.SmtpClient:SmtpClient) [Send-MailMessage], SmtpExcept
   ion
    + FullyQualifiedErrorId : SmtpException,Microsoft.PowerShell.Commands.SendMailMessage

I cannot specify a port either, but it seems to me that this may be another issue since I am hearing back from the server, is there some reason I can't send this email out? I found some things on setting up an SMTP relay, but I don't manage that.

If I use the domain we use for mail instead (somedomain.com), I get a different error messsage about authentication:

Send-MailMessage : The remote certificate is invalid according to the validation procedure.
At C:\ps\FailedJobNotificiation.ps1:16 char:17
+ Send-MailMessage <<<<  -To "myemail@somedomain.com"  -Body $reportHTML -Subject 'Lois Job(s) Failed' -UseSsl -SmtpServ
er 'mail.somedomain.com' -From 'myemail@somedomain.com' -Credential $emailCred
    + CategoryInfo          : InvalidOperation: (System.Net.Mail.SmtpClient:SmtpClient) [Send-MailMessage], Authentica
   tionException
    + FullyQualifiedErrorId : AuthenticationException,Microsoft.PowerShell.Commands.SendMailMessage

With Verbose I get this:

Send-MailMessage : The remote certificate is invalid according to the validation procedure.
At C:\ps\FailedJobNotificiation.ps1:17 char:17
+ Send-MailMessage <<<<  -Verbose -To "myemail@somedomain.com"  -Body $reportHTML -Subject 'Job(s) Failed' -UseSsl
-SmtpServer 'mail.somedomain.com' -From 'myemail@somedomain.com' -Credential $emailCred
    + CategoryInfo          : InvalidOperation: (System.Net.Mail.SmtpClient:SmtpClient) [Send-MailMessage], Authentica
   tionException
    + FullyQualifiedErrorId : AuthenticationException,Microsoft.PowerShell.Commands.SendMailMessage

Best Answer

Review the original error message you received:

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

The first suggestion (requirement of a secure connection) can probably be ignored due to the fact that you did already specify compliance with such a requirement by using the -UseSSL switch parameter

What we're left with, is the impression that the credentials you provided did not successfully authenticate you.

If that is the case, the SMTP Server will treat your identity as "ANONYMOUS", an identity seldom allowed to submit emails unless the sending host is explicitly whitelisted. In this light, the SMTP response message:

5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM

suddenly makes a lot more sense.

My guess is that your SMTP address (myemail@somedomain.com) is not the same as your user principal name (might be myusername@corp.somedomain.com or something similar), which causes authentication to fail

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