(PowerShell) Send Encrypted Email to Multiple Recipients

Demonstrates how to create and send an S/MIME encrypted email to multiple recipients. The digital certificate of each recipient is required. The encrypting/sending process uses each recipient's digital certificate (which internally contains the public key). Each recipient decrypts the received email using his/her private key.

Chilkat .NET Downloads Chilkat .NET Assemblies

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 and receiving email.
$mailman = New-Object Chilkat.MailMan

# Set the SMTP server.
$mailman.SmtpHost = "smtp.mymailserver.com"

# Load each recipient's certificate into a Chilkat certificate object.
# This example loads the certificates from files.  However, the Chilkat
# certificate object provides other means for loading certificates,
# such as from in-memory PEM strings, or in-memory binary DER encoded form, etc.
$cert1 = New-Object Chilkat.Cert
$success = $cert1.LoadFromFile("recipient1.cer")
if ($success -ne $true) {
    $($cert1.LastErrorText)
    exit
}

$cert2 = New-Object Chilkat.Cert
$success = $cert2.LoadFromFile("recipient2.cer")
if ($success -ne $true) {
    $($cert2.LastErrorText)
    exit
}

$cert3 = New-Object Chilkat.Cert
$success = $cert3.LoadFromFile("recipient3.cer")
if ($success -ne $true) {
    $($cert3.LastErrorText)
    exit
}

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

$email.Subject = "This email is encrypted and sent to 3 recipients"
$email.Body = "This is an S/MIME encrypted mail sent to 3 recipients"
$email.From = "Chilkat Support <support@chilkatsoft.com>"

# Make each of the certificates available for encrypting the email
# by calling AddEncryptCert for each.
$success = $email.AddEncryptCert($cert1)
if ($success -eq $true) {
    $success = $email.AddEncryptCert($cert2)
}

if ($success -eq $true) {
    $success = $email.AddEncryptCert($cert3)
}

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

# Add 3 recipients to the email (2 TO addresses, and 1 CC address)
$success = $email.AddTo("Recipient 1","admin@cknotes.com")
$success = $email.AddTo("Recipient 2","somebody001122@yahoo.com")
$success = $email.AddCC("Recipient 3","somebody123xyz@gmail.com")

# Indicate that the email is to be sent encrypted.
$email.SendEncrypted = $true

# Send the encrypted email...
$success = $mailman.SendEmail($email)
if ($success -ne $true) {
    $($mailman.LastErrorText)
}
else {
    $("Encrypted Email Sent!")
}