(PowerShell) Send Email with Hotmail (live.com) -- smtp-mail.outlook.com

Demonstrates the SMTP settings required for sending email through Hotmail (A live.com email address). The Hotmail SMTP server is smtp-mail.outlook.com and receives connections on the SMTP port 587. It expects STARTTLS to establish an explicit TLS connection.

Note: When I first tested this code, I received the following error:

550 5.3.4 554-554 5.2.0 STOREDRV.Deliver; delivery result banner

Mozilla Thunderbird also encountered the same error. I then started a browser, visited outlook.live.com, and logged in to my account. I probably hadn't done that for a very long time. I then retried running this example, and everything worked.

Also, it seems that the SMTP server hostname can be either "smtp-mail.outlook.com" or "smtp.live.com". Both worked.

Chilkat .NET Downloads Chilkat .NET Assemblies Chilkat for Mono

Add-Type -Path "C:\chilkat\ChilkatDotNet47-9.5.0-x64\ChilkatDotNet47.dll"

# This example requires the Chilkat API to have been previously unlocked.
# See Global Unlock Sample for sample code.

# The mailman object is used for sending (SMTP) and receiving (POP3) email.
$mailman = New-Object Chilkat.MailMan

# Set the SMTP server.
# Apparently, both "smtp-mail.outlook.com" and "smtp.live.com" are valid.
$mailman.SmtpHost = "smtp.live.com"
$mailman.SmtpPort = 587

# Set the SMTP login/password (if required)
$mailman.SmtpUsername = "myLogin@live.com"
$mailman.SmtpPassword = "MY-HOTMAIL-PASSWORD"

# Create a new email object
$email = New-Object Chilkat.Email

$email.Subject = "This is a test"
$email.Body = "This is a test"
$email.From = "My Hotmail Account <myLogin@live.com>"
$success = $email.AddTo("Chilkat Admin","admin@chilkatsoft.com")

$success = $mailman.OpenSmtpConnection()
if ($success -ne $true) {
    $($mailman.LastErrorText)
    $("ConnectFailReason = " + $mailman.ConnectFailReason)
    exit
}

$success = $mailman.SmtpAuthenticate()
if ($success -ne $true) {
    $($mailman.LastErrorText)
    exit
}

$success = $mailman.SendEmail($email)
if ($success -ne $true) {
    $($mailman.LastErrorText)
    exit
}

$mailman.CloseSmtpConnection()

$("Email Sent.")