S/MIME interoperability with external clients:
Verified with Microsoft 365/Office 5568.1000 — updated on September 4, 2026
Supported on: At least Windows Server 2008 R2 or Windows 7
Path in the GPO console
User Configuration\Administrative Templates\Microsoft Outlook 2016\Security\Cryptography Description
This policy setting controls whether Outlook decodes encrypted messages itself or passes them to an external program for processing. If you enable this policy setting, you can choose from three options for configuring external S/MIME clients: - Handle internally. Outlook decrypts all S/MIME messages itself. - Handle externally. Outlook hands all S/MIME messages off to the configured external program. - Handle if possible. Outlook attempts to decrypt all S/MIME messages itself. If it cannot decrypt a message, Outlook hands the message off to the configured external program. This option is the default configuration. If you disable or do not configure this policy setting, the behavior is the equivalent of selecting Enabled – Handle if possible.
Registry
HKCU
software\policies\microsoft\office\16.0\outlook\security Export Builder
BETAConfigure the state, scope and options, then generate .reg, PowerShell, Intune and SCCM outputs — or add the setting to a multi-setting collection.
These exports write the registry — this is not a managed GPO. ⓘ
.reg file
Windows Registry Editor Version 5.00
; Exported from gporais.com
; Policy: S/MIME interoperability with external clients:
; State: Enabled
; Supported on: At least Windows Server 2008 R2 or Windows 7
[HKEY_CURRENT_USER\software\policies\microsoft\office\16.0\outlook\security]
"externalsmime"=dword:00000002More formats (PowerShell, Intune, SCCM)
PowerShell
# Exported from gporais.com
# Policy: S/MIME interoperability with external clients:
# State: Enabled
# Supported on: At least Windows Server 2008 R2 or Windows 7
# Warning: In SYSTEM context (the Intune default), HKCU targets the SYSTEM profile. Run this script using the logged-on credentials.
$path = 'HKCU:\software\policies\microsoft\office\16.0\outlook\security'
New-Item -Path $path -Force | Out-Null
Set-ItemProperty -Path $path -Name 'externalsmime' -Value 2 -Type DWordIntune XML
No direct Policy CSP / OMA-URI mapping for this policy. Use the Intune Remediation tab, or ingest the ADMX in Intune.Intune Remediation
# === Detection script ===
# Exported from gporais.com
# Policy: S/MIME interoperability with external clients:
# State: Enabled
# Supported on: At least Windows Server 2008 R2 or Windows 7
# Warning: In SYSTEM context (the Intune default), HKCU targets the SYSTEM profile. Run this script using the logged-on credentials.
function Test-RegistryValue {
param(
[Parameter(Mandatory = $true)][string]$Path,
[Parameter(Mandatory = $true)][string]$Name,
[object]$Expected,
[ValidateSet('String', 'DWord', 'MultiString')][string]$Kind = 'String',
[switch]$Absent
)
try {
$item = Get-ItemProperty -LiteralPath $Path -Name $Name -ErrorAction Stop
} catch {
return $Absent.IsPresent
}
if ($Absent.IsPresent) { return $false }
$actual = $item.$Name
if ($Kind -eq 'DWord') { return ([int64]$actual) -eq ([int64]$Expected) }
if ($Kind -eq 'MultiString') {
$actualValues = @($actual)
$expectedValues = @($Expected)
if ($actualValues.Count -ne $expectedValues.Count) { return $false }
for ($i = 0; $i -lt $expectedValues.Count; $i++) {
if ([string]$actualValues[$i] -ne [string]$expectedValues[$i]) { return $false }
}
return $true
}
return [string]$actual -eq [string]$Expected
}
$checks = @(
(Test-RegistryValue -Path 'HKCU:\software\policies\microsoft\office\16.0\outlook\security' -Name 'externalsmime' -Expected 2 -Kind DWord)
)
if ($checks -notcontains $false) {
Write-Output 'Compliant'
exit 0
}
Write-Output 'Non-compliant'
exit 1
# === Remediation script ===
# Exported from gporais.com
# Policy: S/MIME interoperability with external clients:
# State: Enabled
# Supported on: At least Windows Server 2008 R2 or Windows 7
# Warning: In SYSTEM context (the Intune default), HKCU targets the SYSTEM profile. Run this script using the logged-on credentials.
$path = 'HKCU:\software\policies\microsoft\office\16.0\outlook\security'
New-Item -Path $path -Force | Out-Null
Set-ItemProperty -Path $path -Name 'externalsmime' -Value 2 -Type DWordSCCM scripts
# Exported from gporais.com
# Policy: S/MIME interoperability with external clients:
# State: Enabled
# Supported on: At least Windows Server 2008 R2 or Windows 7
# SCCM Configuration Item guidance:
# Create a Configuration Item of type "Setting: Script".
# Discovery script: use the Detection script below.
# Remediation script: use the Remediation script below.
# Compliance rule: the Discovery script output equals 'Compliant'.
# === Detection script ===
# Exported from gporais.com
# Policy: S/MIME interoperability with external clients:
# State: Enabled
# Supported on: At least Windows Server 2008 R2 or Windows 7
# Warning: In SYSTEM context (the Intune default), HKCU targets the SYSTEM profile. Run this script using the logged-on credentials.
function Test-RegistryValue {
param(
[Parameter(Mandatory = $true)][string]$Path,
[Parameter(Mandatory = $true)][string]$Name,
[object]$Expected,
[ValidateSet('String', 'DWord', 'MultiString')][string]$Kind = 'String',
[switch]$Absent
)
try {
$item = Get-ItemProperty -LiteralPath $Path -Name $Name -ErrorAction Stop
} catch {
return $Absent.IsPresent
}
if ($Absent.IsPresent) { return $false }
$actual = $item.$Name
if ($Kind -eq 'DWord') { return ([int64]$actual) -eq ([int64]$Expected) }
if ($Kind -eq 'MultiString') {
$actualValues = @($actual)
$expectedValues = @($Expected)
if ($actualValues.Count -ne $expectedValues.Count) { return $false }
for ($i = 0; $i -lt $expectedValues.Count; $i++) {
if ([string]$actualValues[$i] -ne [string]$expectedValues[$i]) { return $false }
}
return $true
}
return [string]$actual -eq [string]$Expected
}
$checks = @(
(Test-RegistryValue -Path 'HKCU:\software\policies\microsoft\office\16.0\outlook\security' -Name 'externalsmime' -Expected 2 -Kind DWord)
)
if ($checks -notcontains $false) {
Write-Output 'Compliant'
exit 0
}
Write-Output 'Non-compliant'
exit 1
# === Remediation script ===
# Exported from gporais.com
# Policy: S/MIME interoperability with external clients:
# State: Enabled
# Supported on: At least Windows Server 2008 R2 or Windows 7
# Warning: In SYSTEM context (the Intune default), HKCU targets the SYSTEM profile. Run this script using the logged-on credentials.
$path = 'HKCU:\software\policies\microsoft\office\16.0\outlook\security'
New-Item -Path $path -Force | Out-Null
Set-ItemProperty -Path $path -Name 'externalsmime' -Value 2 -Type DWordBuilding a multi-setting collection? Add this setting and generate combined .reg / PowerShell / GPO scripts.