Send Email from PowerShell - Tutorial¶

Installation¶

EASendMail is a SMTP component which supports all operations of SMTP/ESMTP protocols (RFC 821, RFC 822, RFC 2554). It also supports Exchange Web Service (EWS) and WebDAV protocols. Before you can use the following example codes, you should download the EASendMail Installer and install it on your machine at first.

Then we can use the following codes to load EASendMail to PowerShell script and use it for sending email.

# please change the path to EASendMail Installation Path.
[reflection.assembly]::LoadFile("C:\Program Files (x86)\EASendMail\Lib\net20\EASendMail.dll")

.NET Assembly¶

Because EASendMail has separate builds for .Net Framework, please refer to the following table and choose the correct dll.

Separate builds of run-time assembly for .NET Framework 1.1, 2.0, 3.5, 4.0, 4.5, 4.6.1, .NET Core 2.1 and .NET Compact Framework 2.0, 3.5.

[Send Email from PowerShell - Example]¶

Now let’s create a script named “SendEmailFromPowerShell.ps1” by notepad like this:

notepad SendEmailFromPowerShell.ps1

After notepad is opened, input the following codes and save it.

# To use the following codes, please download and install
# https://www.emailarchitect.net/webapp/download/easendmail.exe on your machine

[reflection.assembly]::LoadFile("C:\Program Files (x86)\EASendMail\Lib\net20\EASendMail.dll")

function SendMailTo($sender, $name, $address, $subject, $body, $htmlFormat) {

    $mail = New-Object EASendMail.SmtpMail("TryIt")
    $mail.From.Address = $sender

    $recipient = New-Object EASendMail.MailAddress($name, $address)
    $mail.To.Add($recipient) > $null

    $mail.Subject = $subject
    if($htmlFormat) {
        $mail.HtmlBody = $body
    }
    else {
        $mail.TextBody = $body
    }

    # please change server, user, password to yours
    $server = New-Object EASendMail.SmtpServer("mail.emailarchitect.net")
    $server.User = "test@emailarchitect.net"
    $server.Password = "yourpassword"

    # If your 25 port is blocked by ISP, you can try to use 587 port
    $server.Port = 25

    # Using TryTLS,
    # If smtp server supports TLS, then TLS connection is used; otherwise, normal TCP connection is used.
    # https://www.emailarchitect.net/easendmail/sdk/?ct=o_smtpconnecttype
    $server.ConnectType = [EASendMail.SmtpConnectType]::ConnectTryTLS

    # If your server is Exchange 2007 or later version, you can use EWS protocol.
    # https://www.emailarchitect.net/easendmail/sdk/?ct=o_serverprotocol
    # Set Exchange Web Service Protocol - EWS - Exchange 2007/2010/2013/2016
    # $server.Protocol = [EASendMail.ServerProtocol]::ExchangeEWS

    $smtp = New-Object EASendMail.SmtpClient
    $smtp.SendMail($server, $mail)
}

function SendMailFromPowerShell () {
    $sender = "test@emailarchitect.net"
    $name = "PowerShell"
    $address = "powershell@appmaildev.com"
    $subject = "Test email from Powershell"
    $body = "This is a test email from Powershell"

    try {
        "Start to send email to {0} ..." -f $address
        SendMailTo $sender $name $address $subject $body ""
        "Email to {0} has been submitted to server!" -f $address
    }
    catch [System.Exception] {
        "Failed to send email: {0}" -f  $_.Exception.Message
    }
}

SendMailFromPowerShell

Run the script like this:

.\SendEmailFromPowerShell.ps1

You will see the status and result in PowerShell Console Output.

Gmail SMTP Server¶

Gmail SMTP server address is smtp.gmail.com. It requires implicit SSL or explicit SSL (TLS) connection, and you should use your Gmail email address as the user name for ESMTP authentication. For example: your email is gmailid@gmail.com, and then the user name should be gmailid@gmail.com.

The Gmail IMAP and SMTP servers have been extended to support authorization via the industry-standard OAuth 2.0 protocol. Using OAUTH protocol, user can do authentication by Gmail Web OAuth instead of inputting user and password directly in application. This way is more secure, but a little bit complex.

Using Gmail SMTP OAUTH

Hotmail/Outlook SMTP Server¶

Hotmail/Live/Outlook.com SMTP server address is smtp.office365.com. It requires explicit SSL (TLS) connection to do user authentication, and you should use your Hotmail/Live/Outlook.com email address as the user name for ESMTP authentication. For example: your email is liveid@hotmail.com, and then the user name should be liveid@hotmail.com.

If your account enabled two-factor authentication, you cannot login your account by normal user authentication, you should use SMTP OAUTH or App Password.

You can generate App Passwords and use this app password instead of your user password.

Office365 SMTP Server¶

By default, Office 365 SMTP server uses 587 port and explicit SSL (TLS) connection.

If your account enabled two-factor authentication, you cannot login your account by normal user authentication, you should use SMTP OAUTH or App Password. You can generate App Passwords and use this app password instead of your user password.

Yahoo SMTP Server¶

Yahoo SMTP server address is smtp.mail.yahoo.com. It supports both Normal/Implicit SSL/Explicit SSL (TLS) connection to do user authentication, and you should use your Yahoo email address as the user name for ESMTP authentication. For example: your email is myid@yahoo.com, and then the user name should be myid@yahoo.com.

If you want to use implicit SSL connection with Yahoo SMTP server, you must set the port to 465.

[PowerShell - Email syntax - Example]¶

Here are some examples:

# From is a MailAddress object, it supports implicit converting from string.
# The syntax is like this: "test@adminsystem.com" or "Tester<test@adminsystem.com>"
# The example code without implicit converting:
$mail = New-Object EASendMail.SmtpMail("TryIt")

$mail.From = New-Object EASendMail.MailAddress("Tester", "test@adminsystem.com")
$mail.From = New-Object EASendMail.MailAddress("Tester<test@adminsystem.com>")
$mail.From = New-Object EASendMail.MailAddress("test@adminsystem.com")

# To, Cc and Bcc is a AddressCollection object, it supports implicit converting
# from string. Multiple addresses are separated with (,;)
# The syntax is like this: "test@adminsystem.com, test1@adminsystem.com"
# The example code without implicit converting:
$mail.To = New-Object EASendMail.AddressCollection("test1@adminsystem.com, test2@adminsystem.com" )
$mail.To = New-Object EASendMail.AddressCollection("Test1<test@adminsystem.com>, Test2<test2@adminsystem.com>")

# You can add more recipient by Add method:
$mail.To.Add((New-Object EASendMail.MailAddress( "tester", "test@adminsystem.com")))

# You can also add carbon copy (CC) or blind carbon copy (BCC) in the email:
$mail.Cc.Add((New-Object EASendMail.MailAddress("CC recipient", "cc@adminsystem.com")))
$mail.Bcc.Add((New-Object EASendMail.MailAddress("Bcc recipient", "bcc@adminsystem.com")))

[PS - From, ReplyTo, Sender and Return-Path in Email - Example]¶

The following example codes demonstrate how to specify From, Reply-To, Sender and Return-Path in Email. With the following example codes:

• If the email couldn’t be delivered to recipient, a non-delivery report will be sent to report@emailarchitect.net.
• If the user received the email, the email client will display: sender@emailarchitect.net on behalf of from@adminsystem.com.
• If the user click “reply”, the replied email will be sent to reply@adminsystem.com.

$mail = New-Object EASendMail.SmtpMail("TryIt")
$mail.From = "from@adminsystem.com"
$mail.ReplyTo = "reply@adminsystem.com"
$mail.Sender = "sender@emailarchitect.net"
$mail.ReturnPath = "report@emailarchitect.net"

“No Such Host” Error¶

This error means DNS server cannot resolve SMTP server, you should check if you input correct server address. If your server address is correct, you should check if your DNS server setting is correct.

Common “Socket/Networking Connection” Error¶

This error means there is a problem with networking connection to SMTP server. You can use Windows built-in Telnet command to detect the networking connection.

Using Telnet to detect networking connection to SMTP server¶

Under DOS command prompt, input “telnet [serveraddress] [port]”:

telnet mail.emailarchitect.net 25
press enter.

If the networking connection to your SMTP server is good, it should return a message like 220 .... If it returns Could not open connection to ..., that means the networking connection to SMTP server is bad, or outbound 25 port is blocked by anti-virus software, firewall or ISP. Please have a look at the following screenshot:

SMTP 25, 587, 465 port¶

25 port is the default SMTP server port to receive email. However, some ISP block outbound 25 port to prevent user to send email directly to other SMTP server. Therefore, many email providers also provide an alternative port 587 to receive email from such users. 465 port is the common port used to receive email over implicit SSL connection. If you use telnet to test 465 port, it doesn’t return the “220…”, because it requires SSL hand shake. But if the connection is ok, telnet returns a flash cursor.

“5xx … IP address block or on black list or bad reputation” Exception¶

This error means SMTP server blocks your IP address or email content. You can try to set user/password in your codes to do user authentication and try it again. If email client set user authentication, most SMTP servers do not check client source IP address in black list.

“5xx user authenticaton” Error¶

TThis error means user authentication is failed, you should check whether you input correct user/password. Password is always case-sensitive.

“5xx relay denied” Error¶

For anti-spam policy, most SMTP servers do not accept the email to outbound domain without user authentication. You should set user/password in the codes and try it again.

“5xx Must issue a STARTTLS command first”¶

This error means SMTP server requires SSL/TLS connection. You should enable SSL/TLS connection like this:

# If your smtp server requires TLS connection, please add this line
$server.ConnectType = [EASendMail.SmtpConnectType]::ConnectSSLAuto;

“No supported authentication marshal found!”¶

This error means SMTP server doesn’t support user authentication or it requires user authentication over SSL/TLS connection. You can try to remove user/password in your codes and try it again.

Other error returned by SMTP server¶

If SMTP server returns an error, it usually returns description about this error. Some descriptions also include a HTTP link, you can go to this linked web page to learn more detail. You can also use the following codes to generate a log file to learn all SMTP session between client and server.

[PS - Using log file to detect SMTP server response - Example]

try
{
    # add this line here to generate log file
    $smtp.LogFileName = "d:\\smtp.txt"
    $smtp.SendMail($server, $mail)
    Write-Host "email was sent successfully!"
}
catch [System.Exception] {
    "Failed to send email: {0}" -f  $_.Exception.Message
}