Windows SMTP: Script Outbound Security

Question

Building a config script in PowerShell to configure web servers' SMTP service to use the AWS SES (simple email service) for outbound mail delivery. Easy to do manually, but as we enter a load-balanced world, I'm having a helluva time getting it scripted.

My main challenge seems to be turning on Basic Auth and providing the creds. I can't seem to figure out what WMI fields those might be... I'm thinking the cred fields are RouteUserName and RoutePassword, but can't seem to find the right option to turn on BasicAuth to prove that. Checking the TLS encryption box is evading me as well.

Am I missing something obvious or just not using the right variables?

Fields I'm struggling with illustrated:

Sample script that I've built so far. Relay IP works and the RouteUserName and RoutePassword fields are confirmed set. But what are the rest?

$smtpuser = Get-SSMParameter -Name SMTP_User
$smtppass = Get-SSMParameter -Name SMTP_Password -WithDecryption $true
$smtpfqdn = "$env:computername.$env:userdnsdomain"

$SmtpConfig = Get-WMIObject -Namespace root/MicrosoftIISv2 -ComputerName localhost -Query "Select * From IisSmtpServerSetting"
$RelayIpList = @( 24, 0, 0, 128, 32, 0, 0, 128, 60, 0, 0, 128, 68, 0, 0, 128, 1, 0, 0, 0, 76, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 1, 0, 0, 0, 1, 0, 0, 0, 2, 0, 0, 0, 2, 0, 0, 0, 4, 0, 0, 0, 0, 0, 0, 0, 76, 0, 0, 128, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 255, 255, 255, 255, 127, 0, 0, 1 )
$SmtpConfig.RelayIPList = $RelayIPList
$SmtpConfig.AllowAnonymous = $false
$SmtpConfig.AuthBasic = $true
$SmtpConfig.RouteUserName = $smtpuser.Value
$SmtpConfig.RoutePassword = $smtppass.Value
$SmtpConfig.AlwaysUseSsl = $true
$SmtpConfig.DefaultDomain = $smtpfqdn
$SmtpConfig.SmartHost = "email-smtp.us-west-2.amazonaws.com"

$SmtpConfig.Put()

Restart-Service "SMTPSVC" -ErrorAction

score 3 · Accepted Answer · answered Jun 24 '19 at 18:17

Solved with much experimentation. Here's the pertinent bits of my script. Note that I'm keeping the SMTP user creds stored in AWS Systems Manager parameter store.

$smtpuser = Get-SSMParameter -Name SMTP_User
$smtppass = Get-SSMParameter -Name SMTP_Password -WithDecryption $true
$smtpfqdn = "$env:computername.$env:userdnsdomain"

Set-Service "SMTPSVC" -StartupType Automatic -ErrorAction SilentlyContinue
Start-Service "SMTPSVC" -ErrorAction SilentlyContinue

$SmtpConfig = Get-WMIObject -Namespace root/MicrosoftIISv2 -ComputerName localhost -Query "Select * From IisSmtpServerSetting"
$RelayIpList = @( 24, 0, 0, 128, 32, 0, 0, 128, 60, 0, 0, 128, 68, 0, 0, 128, 1, 0, 0, 0, 76, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 1, 0, 0, 0, 1, 0, 0, 0, 2, 0, 0, 0, 2, 0, 0, 0, 4, 0, 0, 0, 0, 0, 0, 0, 76, 0, 0, 128, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 255, 255, 255, 255, 127, 0, 0, 1 )
$SmtpConfig.RelayIPList = $RelayIPList
$SmtpConfig.AuthFlags = "1"
$SmtpConfig.AuthBasic = $false
$SmtpConfig.RouteAction = "268"
$SmtpConfig.RouteUserName = $smtpuser.Value
$SmtpConfig.RoutePassword = $smtppass.Value
$SmtpConfig.AlwaysUseSsl = $true
$SmtpConfig.SmartHostType = "2"
$SmtpConfig.DefaultDomain = $smtpfqdn
$SmtpConfig.SmartHost = "email-smtp.us-west-2.amazonaws.com"
$SmtpConfig.RemoteSmtpPort = "587"

$SmtpConfig.Put()

Restart-Service "SMTPSVC" -ErrorAction SilentlyContinue

Windows SMTP: Script Outbound Security

1 Answers1