Sending E-mail from Powershell Failing on One Machine - powershell

I have a bit of powershell to send an e-mail:
$smtp = new-object Net.Mail.SmtpClient($smtpServer)
$smtp.Send($emailFrom, $emailTo, $subject, $body)
This works perfectly on every machine I've ever tried it on until today. I have one machine where I get this error message:
Exception calling "Send" with "4" argument(s): "Failure sending mail."
At R:\sqlrestore\scripts\Utilities\Check-Lag.ps1:15 char:12
+ $smtp.Send <<<< ($emailFrom, $emailTo, $subject, $body)
+ CategoryInfo : NotSpecified: (:) [], ParentContainsErrorRecordException
+ FullyQualifiedErrorId : DotNetMethodException

The error message is ambiguous. It turns out the issue is that the SMTP server was inaccessible because outbound SMTP traffic was not allowed.

By the way, if you're using PowerShell 2.0 then you may want to try the Send-MailMessage cmdlet:
Send-MailMessage -SmtpServer YourServerName -From $emailFrom -To $emailTo -Subject $subject -Body $body

I have just come across the same problem, turns out it was because of two factor authentication. I created a 'app specific password' in Google security settings and all works fine now.

Related

Why does Send-MailMessage fail to send using STARTTLS over Port 587

Why does sending an email message from PowerShell with the Send-MailMessage command using the flag -Port 587 produce an error.
Command:
Send-Mailmessage -smtpServer mail.server.com -Port 587 -from "admin#domain.com" -to "user#domain.com" -subject "Test" -body "Test"
Error Message:
Send-Mailmessage : The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.0 Must issue a STARTTLS command first
The PowerShell documentation says adding -UseSSL should specify that a STARTTLS command be sent, but even adding this flag may not resolve your issues.
Command:
Send-Mailmessage -smtpServer mail.server.com -Port 587 -UseSsl -from "admin#domain.com" -to "user#domain.com" -subject "Test" -body "Test"
Eror message:
Send-Mailmessage : Unable to read data from the transport connection: An existing connection was forcibly closed by the remote host.
Some SMTP servers may have been hardened to only accept TLS 1.2 for negotiating STARTTLS. In many cases Windows is configured to send TLS 1.0 by default when -UseSSL is specified.
To force Send-MailMessage to use TLS 1.2 it is necessary to add a line to the script before executing the Send-MailMessage:
Either enter:
[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12
or
[System.Net.ServicePointManager]::SecurityProtocol = 'TLS12'
If it helps anybody, this post will be worthwhile.
Using Online Exchange via Office 365, this is what I ended up with:
(Sanitized)
$EmailFrom = “[email address]#[FQDN]”
$EmailTo = “[email address]#[FQDN]”
$Subject = “Test email”
$Body = “What do you want your email to say”
$Attachment = "C:\sendmail\test.txt"
$SMTPServer = “smtp.office365.com”
$SMTPClient = New-Object Net.Mail.SmtpClient($SmtpServer, 587)
$SMTPClient.EnableSsl = $true
$attach = new-object Net.Mail.Attachment($Attachment)
$message.Attachments.Add($attach)
$SMTPClient.Credentials = New-Object System.Net.NetworkCredential(“[valid/authorised user name]”, “[password]”);
$SMTPClient.Send($EmailFrom, $EmailTo, $Subject, $Body)
Because I am NOT sending this from an IP Address covered by the SPF record, I have had to authenticate. If the source IP address is covered by the SPF txt record, my understanding is that authentication of user/password would NOT be required (Has not been tested).
Thanks for an awesome article. Was easy to follow, and easy to combine the articles for different requirements in to one, as per the above PowerShell script.
My solution to "5.7.3 STARTTLS is required to send mail" was simple. The domain name for network credentials is case sensitive and had to be all CAPS.

Not receiving email sent using powershell command

Send-MailMessage -SmtpServer "smtp.com.au" -From "me#me.com" -To "you#you.com" -Subject "Testing" -Attachments "\\Test\archive.zip" -Body "attached"
I am using the above command to email a zip file but i don't see anything in the To (you#you.com) mailbox.
The command runs successfully without any errors.
I think the problem is in your function call. You miss a lot of parameters. Take a look on my working gmail example:
$password = ConvertTo-SecureString "123456789" -AsPlainText -Force
$emailCredentials = New-Object pscredential ("from#gmail.com", $password)
try {
Send-MailMessage -From "from#gmail.com" -To "to#to.com" -Subject "subject" -Body "body" -SmtpServer "smtp.gmail.com" -Port 587 -Credential $emailCredentials -Encoding UTF8 -UseSsl -ErrorAction Stop
}
catch {
echo $error[0]
}
There is no -Credential parameter in your call, and I'm almost sure, that's the problem. Also your smtp server may have this protocol on different port, this is what -Port is for. And finally -UseSsl, if smtp server is encrypting mails, then without this switch, your emails will be not send. -Encoding UTF8 is just for regional chars.
Check your $error[0], it may tell you, where the problem is. Check what is happening on your -From email. On gmail you can see sometimes auto-repiles, with error description.
I'm sorry for not giving you simple solution, but I don't have enough informations, to find it.
Ok guys i have an update:
My command mentioned above is working absolutely fine. IT team has told me that we had issues with our SMTP the other day (When i had reported this issue) the emails eventually did come in (too late). I have tested the same this morning and it seems to be fine so a big thanks to all for your support.
I have got another question but i will post it separately.

Localhost SMTP server on Windows Server 2012 R2 Standard not working

Newly installed Windows Server 2012 R2 Standard. I set up SMTP server by this tutorial http://www.vsysad.com/2012/04/setup-and-configure-smtp-server-on-windows-server-2008-r2/ Tested using this powershell command:
Send-MailMessage -SMTPServer localhost -To receiver_mail -From sender_mail -Subject "This is a test email" -Body "Hi Japinator, this is a test email sent via PowerShell"
It worked for some time, but accidentally stopped working at the moment. Tried to review tutorial step-by-step - everything is ok. Receiving this error message when testing in powershell:
Send-MailMessage : Unable to connect to the remote server
At line:1 char:1
+ Send-MailMessage -SMTPServer localhost -To receiver_email -From sender_email ...
+ ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
+ CategoryInfo : InvalidOperation: (System.Net.Mail.SmtpClient:SmtpClient) [
ion
+ FullyQualifiedErrorId : SmtpException,Microsoft.PowerShell.Commands.SendMailMessage
As the answer above alludes to, the issue is due to the SMTP service not being started.
I stopped the SMTP Service on my 2012 test server and then ran the Send-MailMessage command and confirmed that the error was the same:
PS C:\Users\Admin> Send-MailMessage -SMTPServer localhost -To xxxxxxxxx#gmail.com -From blog#vsysad.com
-Subject "This is a test email" -Body "Hi, this is a test email sent via PowerShell"
Send-MailMessage : Unable to connect to the remote server
At line:1 char:1
+ Send-MailMessage -SMTPServer localhost -To xxxxxxxxx#gmail.com -From blog#vsysad ...
+ ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
+ CategoryInfo : InvalidOperation: (System.Net.Mail.SmtpClient:SmtpClient) [Send-MailMessage], SmtpExcept
ion
+ FullyQualifiedErrorId : SmtpException,Microsoft.PowerShell.Commands.SendMailMessage
The first thing to do would be to check whether the service is running:
PS C:\Users\Admin> get-service smtpsvc
Status Name DisplayName
------ ---- -----------
Stopped smtpsvc Simple Mail Transfer Protocol (SMTP)
Per the above, if the SMTP Service is not running then run the command below to start it:
PS C:\Users\Admin> start-service smtpsvc
Then set the startup to Automatic. Run the command below to do this:
PS C:\Users\Admin> set-service smtpsvc -StartupType Automatic
This will ensure that the SMTP service starts up automatically when the server boots up.
Your SMTP server should now be able to process your Send-mailMessage request and assuming the rest of the config is sound, relay the message successfully.
SMTP Virtual Server On IIS6 was not started. By default it doest not start automatically. Autostart can be done according this thread https://serverfault.com/questions/263546/automatically-start-smtp-server-in-iis

Learning an Email script using Gmail SMTP authentication

I'm new to power shell scripting.I wrote a script which should send an email to my inbox
I found few solution and improved my script
$cred = Get-Credential
Send-MailMessage -SmtpServer "smtp-relay.gmail.com" -Credential $cred -UseSsl -Port 587 -From "test#gmail.com" -To "test#gmail.com" -Subject "test" -Body "test"
I got an error message as follows below
Send-MailMessage : Mailbox unavailable. The server response was: 5.7.0 Mail relay denied
[117.193.79.33]. bd10sm271633igb.4 - gsmtp
At line:2 char:1
+ Send-MailMessage -SmtpServer "smtp-relay.gmail.com" -Credential $cred -UseSsl -P ...
+ ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
+ CategoryInfo : InvalidOperation: (System.Net.Mail.SmtpClient:SmtpClient) [Send-M
ailMessage], SmtpException
+ FullyQualifiedErrorId : SmtpException,Microsoft.PowerShell.Commands.SendMailMessage
Again I changed the port number 465 or 25,it get operation timeout.Help me out!!
PS:Telnet on 25 or 587 is working and no AV program in computer
Thanks in advance.
$cred = Get-Credential Send-MailMessage -SmtpServer "smtp.gmail.com" -Credential $cred -UseSsl -Port 587 -From "test#gmail.com" -To "test#gmail.com" -Subject "test" -Body "test"
This Testing with Gmail works,after i followed this steps
1.Disable two way verification
2.Allow less secure apps in settings
Lesssecure Apps

Trouble sending email using Powershell

I've run the following script:
PS C:\> Send-MailMessage -To <EmailAddress1> -From <EmailAddress2> -Body "This is a test" -Subject "TEST MAIL" -SmtpServer <INTERNAL IP OF SMTP SERVER>
And I receive the following error:
Send-MailMessage : Unable to read data from the transport connection: net_io_connectionclosed.
At line:1 char:17
+ Send-MailMessage <<<< -To <EmailAddress1> -From <EmailAddress2> -Body "This is a test" -Subject "TEST MAIL" -SmtpServer <INTERNAL IP OF SMTP SERVER>
+ CategoryInfo: InvalidOperation: (System.Net.Mail.SmtpClient:SmtpClient) [Send-Mail Message], SmtpException
+ FullyQualifiedErrorId : SmtpException,Microsoft.PowerShell.Commands.SendMailMessage`
I was made aware of the fact that I need permissions to send email from my local machine through the SMTP server, and as far as I know, I've been granted those rights.
Would somebody please help point me in the right direction on this one?
The ultimate goal is to be able to send emails as part of some Powershell scripts.
Thanks!
I prefer the Net.Mail.SmtpClient method of sending email. This script would send the contents of a file passed as a parameter.
$emailFrom = "AUTOMATED_PRERUN#somehost.com"
$emailTo = "somebody#somehost.com"
$subject = "TEST"
get-content $Args[0] | %{$Body+= " {0} `n" -f $_}
$smtpServer = "mailserver.somehost.com"
$smtp = new-object Net.Mail.SmtpClient($smtpServer)
$smtp.Send($emailFrom, $emailTo, $subject, $body)
Though, your error sounds more like a networking issue of some type.
You might want to check that you can reach the SMTP port on the server:
https://learn.microsoft.com/en-us/Exchange/mail-flow/test-smtp-with-telnet
Probably your antivirus file service is locking mail delivery.