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Cause of a Powershell Scripting Error for sending email with attachment

E=mc2
E=mc2 asked
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Last Modified: 2018-10-15
What would cause this type of error in a Powershell script?

Send-MailMessage : The operation has timed out.
At C:\Users\Name\Desktop\Folder\script.ps1:17 char:1
+ Send-MailMessage @sendMailArgs
+ ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
    + CategoryInfo          : InvalidOperation: (System.Net.Mail.SmtpClient:SmtpClient) [Send-MailMessage], SmtpExcept
   ion
    + FullyQualifiedErrorId : SmtpException,Microsoft.PowerShell.Commands.SendMailMessage
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Tahir QureshiSystem Analyst

Commented:
you have to share your script Plus what command you are using
plus check smtp port is open or not
MichelangeloSystem Administrator / Postmaster
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Commented:
Check the SMTP server address: is it correct?is Port 25 reachable from where the script is running? As Tahir advised, provide more details.

Author

Commented:
The port is open, since I am able to use the following script however it's successful only when I use it without the attachment.


$username = 'email1@gmail.com'
$password = 'password'
$sendMailArgs = @{
      To =                  'email2@gmail.com'
      From =                  $username
      Cc =                  'email3@gmail.com'
    Bcc =           'email1@hotmail.com'
      Subject =            'File as Attached'
      Body =                  'The file is attached'
      Attachments =      'C:\Users\User1\Desktop\Folder\File.pdf'
      SmtpServer =      'smtp.gmail.com'
      Port =                  587
      UseSsl =            $true
      Credential =      New-Object -TypeName System.Management.Automation.PSCredential -ArgumentList $username, (ConvertTo-SecureString $password -AsPlaintext -Force)
}
Send-MailMessage @sendMailArgs
Write-Host "Mail Sent"
"Batchelor", Developer and EE Topic Advisor
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Top Expert 2015
Commented:
This problem has been solved!
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Author

Commented:
Outlook works fine.
And I even renamed the attachment and it still did not work.
Jose Gabriel Ortega CastroTop-Rated Plus Freelancer (Upwork)/EE Solution Guide / CEO / Photographer
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Awarded 2018
Distinguished Expert 2018

Commented:
I've done it 2 ways:

$username = 'jortega928@gmail.com'
$password = 'xxx'
 

$smtp = new-object Net.Mail.SmtpClient('smtp.gmail.com') 
$smtp.EnableSsl = $true 
$msg = new-object Net.Mail.MailMessage  

$msg.From = $username
$msg.To.Add("jortega@faboit.com") 
$msg.BodyEncoding = [system.Text.Encoding]::Unicode 
$msg.SubjectEncoding = [system.Text.Encoding]::Unicode 
$msg.IsBodyHTML = $true  
$msg.Subject = "File is Attached" 
$msg.Body = "The file is attached"
$msg.Attachments.Add("Z:\WORKING_DIR\file1.csv")

try{
$SMTP.Credentials = New-Object System.Net.NetworkCredential("$username", "$password"); 
$smtp.Send($msg)
}
catch{
    $er = $_.Exception.Message
    Write-Error $_.Exception.Message
}

Open in new window


(Other way):
try{
    $From = "jortega928@gmail.com"
    $To = "jortega@faboit.com"
    $Cc = "ceo@faboit.com"
    $Attachment = "Z:\WORKING_DIR\file1.csv"
    $Subject = "Email Subject"
    $Body = "Insert body text here"
    $SMTPServer = "smtp.gmail.com"
    $SMTPPort = "587"
    Send-MailMessage -From $From -to $To -Cc $Cc -Subject $Subject `
    -Body $Body -SmtpServer $SMTPServer -port $SMTPPort -UseSsl `
    -Credential (Get-Credential -UserName $From -Message "Insert the password for $From") -Attachments $Attachment
}
catch{
    Write-Error $_.Exception.Message
}

Open in new window


I get the following "The SMTP server requires a secure connection or the client was not authenticated.
error 5.5.1 (Authentication required).


This is because I have disabled this  (Less secure app) when I enabled it works.
https://myaccount.google.com/lesssecureapps

If you ask me I'd use the second since I wouldn't need to hardcode my password on the script ;)

Author

Commented:
The smtp server was rejecting.

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