Hello folks, today I want to present you my another product in PKI integration with Windows PowerShell. I worked hard on server-side extensions: PowerShell PKI Module, which is (so far) the biggest project I have developed.

Now I got a time to work on client side extensions. Some prototypes are already published in this blog. The first complete tool (which is a part of client-side extensions) is self-signed certificate creation for testing purposes. The reason why I developed this tool is that makecert.exe (from Windows SDK) is now deprecated. The blog post provides a replacement for makecert — certreq.exe tool. Although, certreq is very cool, there are few things to note:

1. certreq uses external INF file which may be a bit complicated.
2. if there is a mistake in the INF file, certreq raises exception message box. It is a pain when the message box is raised in PowerShell remoting session. You never will see it and unable to close it!

My script relies on the same APIs as certreq and more flexible. Also it demonstrates the techniques of CertEnroll API usage in action.

The script defines the following parameters:

• Subject — specifies the certificate subject in a X500 distinguished name format. Example: CN=Test Cert, OU=Sandbox
• NotBefore — Specifies the date and time when the certificate become valid. By default previous day date is used.
• NotAfter — Specifies the date and time when the certificate expires. By default, the certificate is valid for 1 year.
• SerialNumber — Specifies the desired serial number in a hex format. Example: 01a4ff2
• ProviderName — Specifies the Cryptography Service Provider (CSP) name. You can use either legacy CSP and Key Storage Providers (KSP). By default "Microsoft Enhanced Cryptographic Provider v1.0" CSP is used.
• AlgorithmName — Specifies the public key algorithm. By default RSA algorithm is used. RSA is the only algorithm supported by legacy CSPs. With key storage providers (KSP) you can use CNG algorithms, like ECDH. For CNG algorithms you must use full name:
  ECDH_P256
  ECDH_P384
  ECDH_P521
  
  In addition, KeyLength parameter must be specified explicitly when non-RSA algorithm is used.
• KeyLength — Specifies the key length to generate. By default 2048-bit key is generated.
• KeySpec — Specifies the public key operations type. The possible values are: Exchange and Signature. Default value is Exchange.
• EnhancedKeyUsage — Specifies the intended uses of the public key contained in a certificate. You can specify either, EKU friendly name (for example 'Server Authentication') or object identifier (OID) value (for example '1.3.6.1.5.5.7.3.1').
• KeyUsage — Specifies restrictions on the operations that can be performed by the public key contained in the certificate. Possible values (and their respective integer values to make bitwise operations) are:
  EncipherOnly
  CrlSign
  KeyCertSign
  KeyAgreement
  DataEncipherment
  KeyEncipherment
  NonRepudiation
  DigitalSignature
  DecipherOnly
  
  you can combine key usages values by using bitwise OR operation. when combining multiple flags, they must be enclosed in quotes and separated by a comma character. For example, to combine KeyEncipherment and DigitalSignature flags you should type: "KeyEncipherment, DigitalSignature".
  
  If the certificate is CA certificate (see IsCA parameter), key usages extension is generated automatically with the following key usages: Certificate Signing, Off-line CRL Signing, CRL Signing.
• SubjectAlternativeName — Specifies alternative names for the subject. Unlike Subject field, this extension allows to specify more than one name. Also, multiple types of alternative names are supported. The cmdlet supports the following SAN types:
  RFC822 Name
  IP address (both, IPv4 and IPv6)
  Guid
  Directory name
  DNS name

• IsCA — Specifies whether the certificate is CA (IsCA = $true) or end entity (IsCA = $false) certificate. If this parameter is set to $false, PathLength parameter is ignored. Basic Constraints extension is marked as critical.

• PathLength — Specifies the number of additional CA certificates in the chain under this certificate. If PathLength parameter is set to zero, then no additional (subordinate) CA certificates are permitted under this CA.

• CustomExtension — Specifies the custom extension to include to a self-signed certificate. This parameter must not be used to specify the extension that is supported via other parameters. In order to use this parameter, the extension must be formed in a collection of initialized X509Extension objects.

• SignatureAlgorithm — Specifies signature algorithm used to sign the certificate. By default 'SHA1' algorithm is used.

• FriendlyName — Specifies friendly name for the certificate.

• StoreLocation — Specifies the store location to store self-signed certificate. Possible values are: 'CurrentUser' and 'LocalMachine'. 'CurrentUser' store is intended for user certificates and computer (as well as CA) certificates must be stored in 'LocalMachine' store.

• StoreName — Specifies the container name in the certificate store. Possible container names are:
  AddressBook
  AuthRoot
  CertificateAuthority
  Disallowed
  My
  Root
  TrustedPeople
  TrustedPublisher

• Path — Specifies the path to a PFX file to export a self-signed certificate.

• Password — Specifies the password for PFX file.

• AllowSMIME — Enables Secure/Multipurpose Internet Mail Extensions for the certificate.

• Exportable — Marks private key as exportable. Smart card providers usually do not allow
  exportable keys.

And several useful examples:

New-SelfsignedCertificateEx -Subject "CN=Test Code Signing" -EKU "Code Signing" -KeySpec "Signature" `-KeyUsage
 "DigitalSignature" -FriendlyName "Test code signing" -NotAfter [datetime]::now.AddYears(5)

Creates a self-signed certificate intended for code signing and which is valid for 5 years. Certificate is saved in the Personal store of the current user account.

New-SelfsignedCertificateEx -Subject "CN=www.domain.com" -EKU "Server Authentication", "Client authentication" `-KeyUsage
 "KeyEcipherment, DigitalSignature" -SAN "sub.domain.com","www.domain.com","192.168.1.1" `-AllowSMIME
 -Path C:\test\ssl.pfx -Password (ConvertTo-SecureString "P@ssw0rd" -AsPlainText -Force) -Exportable `-StoreLocation
 "LocalMachine"

Creates a self-signed SSL certificate with multiple subject names and saves it to a file. Additionally, the certificate is saved in the Personal store of the Local Machine store. Private key is marked as exportable, so you can export the certificate with a associated private key to a file at any time. The certificate includes SMIME capabilities.

New-SelfsignedCertificateEx -Subject "CN=www.domain.com" -EKU "Server Authentication", "Client authentication" `-KeyUsage
 "KeyEcipherment, DigitalSignature" -SAN "sub.domain.com","www.domain.com","192.168.1.1" `-StoreLocation
 "LocalMachine" -ProviderName "Microsoft Software Key Storae Provider" -AlgorithmName ecdh_256 `-KeyLength
 256 -SignatureAlgorithm sha256

Creates a self-signed SSL certificate with multiple subject names and saves it to a file. Additionally, the certificate is saved in the Personal store of the Local Machine store. Private key is marked as exportable, so you can export the certificate with a associated private key to a file at any time. Certificate uses Elliptic Curve Cryptography (ECC) key algorithm ECDH with 256-bit key. The certificate is signed by using SHA256 algorithm.

New-SelfsignedCertificateEx -Subject "CN=Test Root CA, OU=Sandbox" -IsCA $true -ProviderName `"Microsoft
 Software Key Storage Provider -Exportable

Creates self-signed root CA certificate.

Here is the code of the script. If you don’t want to read all this mess, scroll down and download ready file:

#####################################################################
# New-SelfSignedCertificateEx.ps1
# Version 1.6
#
# Creates self-signed certificate. This tool is a base replacement
# for deprecated makecert.exe
#
# Vadims Podans (c) 2013
# http://en-us.sysadmins.lv/
#####################################################################
#requires -Version 3.0

function New-SelfSignedCertificateEx {
[CmdletBinding(DefaultParameterSetName = '__store')]
    param (
        [Parameter(Mandatory = $true, Position = 0)]
        [string]$Subject,
        [Parameter(Position = 1)]
        [datetime]$NotBefore = [DateTime]::Now.AddDays(-1),
        [Parameter(Position = 2)]
        [datetime]$NotAfter = $NotBefore.AddDays(365),
        [string]$SerialNumber,
        [Alias('CSP')]
        [string]$ProviderName = "Microsoft Enhanced Cryptographic Provider v1.0",
        [string]$AlgorithmName = "RSA",
        [int]$KeyLength = 2048,
        [validateSet("Exchange","Signature")]
        [string]$KeySpec = "Exchange",
        [Alias('EKU')]
        [Security.Cryptography.Oid[]]$EnhancedKeyUsage,
        [Alias('KU')]
        [Security.Cryptography.X509Certificates.X509KeyUsageFlags]$KeyUsage,
        [Alias('SAN')]
        [String[]]$SubjectAlternativeName,
        [bool]$IsCA,
        [int]$PathLength = -1,
        [Security.Cryptography.X509Certificates.X509ExtensionCollection]$CustomExtension,
        [ValidateSet('MD5','SHA1','SHA256','SHA384','SHA512')]
        [string]$SignatureAlgorithm = "SHA1",
        [string]$FriendlyName,
        [Parameter(ParameterSetName = '__store')]
        [Security.Cryptography.X509Certificates.StoreLocation]$StoreLocation = "CurrentUser",
        [Parameter(Mandatory = $true, ParameterSetName = '__file')]
        [Alias('OutFile','OutPath','Out')]
        [IO.FileInfo]$Path,
        [Parameter(Mandatory = $true, ParameterSetName = '__file')]
        [Security.SecureString]$Password,
        [switch]$AllowSMIME,
        [switch]$Exportable
    )
    $ErrorActionPreference = "Stop"
    if ([Environment]::OSVersion.Version.Major -lt 6) {
        $NotSupported = New-Object NotSupportedException -ArgumentList "Windows XP and Windows Server 2003 are not supported!"
        throw $NotSupported
    }
    $ExtensionsToAdd = @()

#region constants
    # contexts
    New-Variable -Name UserContext -Value 0x1 -Option Constant
    New-Variable -Name MachineContext -Value 0x2 -Option Constant
    # encoding
    New-Variable -Name Base64Header -Value 0x0 -Option Constant
    New-Variable -Name Base64 -Value 0x1 -Option Constant
    New-Variable -Name Binary -Value 0x3 -Option Constant
    New-Variable -Name Base64RequestHeader -Value 0x4 -Option Constant
    # SANs
    New-Variable -Name OtherName -Value 0x1 -Option Constant
    New-Variable -Name RFC822Name -Value 0x2 -Option Constant
    New-Variable -Name DNSName -Value 0x3 -Option Constant
    New-Variable -Name DirectoryName -Value 0x5 -Option Constant
    New-Variable -Name URL -Value 0x7 -Option Constant
    New-Variable -Name IPAddress -Value 0x8 -Option Constant
    New-Variable -Name RegisteredID -Value 0x9 -Option Constant
    New-Variable -Name Guid -Value 0xa -Option Constant
    New-Variable -Name UPN -Value 0xb -Option Constant
    # installation options
    New-Variable -Name AllowNone -Value 0x0 -Option Constant
    New-Variable -Name AllowNoOutstandingRequest -Value 0x1 -Option Constant
    New-Variable -Name AllowUntrustedCertificate -Value 0x2 -Option Constant
    New-Variable -Name AllowUntrustedRoot -Value 0x4 -Option Constant
    # PFX export options
    New-Variable -Name PFXExportEEOnly -Value 0x0 -Option Constant
    New-Variable -Name PFXExportChainNoRoot -Value 0x1 -Option Constant
    New-Variable -Name PFXExportChainWithRoot -Value 0x2 -Option Constant
#endregion
    
#region Subject processing
    # http://msdn.microsoft.com/en-us/library/aa377051(VS.85).aspx
    $SubjectDN = New-Object -ComObject X509Enrollment.CX500DistinguishedName
    $SubjectDN.Encode($Subject, 0x0)
#endregion

#region Extensions

#region Enhanced Key Usages processing
    if ($EnhancedKeyUsage) {
        $OIDs = New-Object -ComObject X509Enrollment.CObjectIDs
        $EnhancedKeyUsage | %{
            $OID = New-Object -ComObject X509Enrollment.CObjectID
            $OID.InitializeFromValue($_.Value)
            # http://msdn.microsoft.com/en-us/library/aa376785(VS.85).aspx
            $OIDs.Add($OID)
        }
        # http://msdn.microsoft.com/en-us/library/aa378132(VS.85).aspx
        $EKU = New-Object -ComObject X509Enrollment.CX509ExtensionEnhancedKeyUsage
        $EKU.InitializeEncode($OIDs)
        $ExtensionsToAdd += "EKU"
    }
#endregion

#region Key Usages processing
    if ($KeyUsage -ne $null) {
        $KU = New-Object -ComObject X509Enrollment.CX509ExtensionKeyUsage
        $KU.InitializeEncode([int]$KeyUsage)
        $KU.Critical = $true
        $ExtensionsToAdd += "KU"
    }
#endregion

#region Basic Constraints processing
    if ($PSBoundParameters.Keys.Contains("IsCA")) {
        # http://msdn.microsoft.com/en-us/library/aa378108(v=vs.85).aspx
        $BasicConstraints = New-Object -ComObject X509Enrollment.CX509ExtensionBasicConstraints
        if (!$IsCA) {$PathLength = -1}
        $BasicConstraints.InitializeEncode($IsCA,$PathLength)
        $BasicConstraints.Critical = $IsCA
        $ExtensionsToAdd += "BasicConstraints"
    }
#endregion

#region SAN processing
    if ($SubjectAlternativeName) {
        $SAN = New-Object -ComObject X509Enrollment.CX509ExtensionAlternativeNames
        $Names = New-Object -ComObject X509Enrollment.CAlternativeNames
        foreach ($altname in $SubjectAlternativeName) {
            $Name = New-Object -ComObject X509Enrollment.CAlternativeName
            if ($altname.Contains("@")) {
                $Name.InitializeFromString($RFC822Name,$altname)
            } else {
                try {
                    $Bytes = [Net.IPAddress]::Parse($altname).GetAddressBytes()
                    $Name.InitializeFromRawData($IPAddress,$Base64,[Convert]::ToBase64String($Bytes))
                } catch {
                    try {
                        $Bytes = [Guid]::Parse($altname).ToByteArray()
                        $Name.InitializeFromRawData($Guid,$Base64,[Convert]::ToBase64String($Bytes))
                    } catch {
                        try {
                            $Bytes = ([Security.Cryptography.X509Certificates.X500DistinguishedName]$altname).RawData
                            $Name.InitializeFromRawData($DirectoryName,$Base64,[Convert]::ToBase64String($Bytes))
                        } catch {$Name.InitializeFromString($DNSName,$altname)}
                    }
                }
            }
            $Names.Add($Name)
        }
        $SAN.InitializeEncode($Names)
        $ExtensionsToAdd += "SAN"
    }
#endregion

#region Custom Extensions
    if ($CustomExtension) {
        $count = 0
        foreach ($ext in $CustomExtension) {
            # http://msdn.microsoft.com/en-us/library/aa378077(v=vs.85).aspx
            $Extension = New-Object -ComObject X509Enrollment.CX509Extension
            $EOID = New-Object -ComObject X509Enrollment.CObjectId
            $EOID.InitializeFromValue($ext.Oid.Value)
            $EValue = [Convert]::ToBase64String($ext.RawData)
            $Extension.Initialize($EOID,$Base64,$EValue)
            $Extension.Critical = $ext.Critical
            New-Variable -Name ("ext" + $count) -Value $Extension
            $ExtensionsToAdd += ("ext" + $count)
            $count++
        }
    }
#endregion

#endregion

#region Private Key
    # http://msdn.microsoft.com/en-us/library/aa378921(VS.85).aspx
    $PrivateKey = New-Object -ComObject X509Enrollment.CX509PrivateKey
    $PrivateKey.ProviderName = $ProviderName
    $AlgID = New-Object -ComObject X509Enrollment.CObjectId
    $AlgID.InitializeFromValue(([Security.Cryptography.Oid]$AlgorithmName).Value)
    $PrivateKey.Algorithm = $AlgID
    # http://msdn.microsoft.com/en-us/library/aa379409(VS.85).aspx
    $PrivateKey.KeySpec = switch ($KeySpec) {"Exchange" {1}; "Signature" {2}}
    $PrivateKey.Length = $KeyLength
    # key will be stored in current user certificate store
    switch ($PSCmdlet.ParameterSetName) {
        '__store' {
            $PrivateKey.MachineContext = if ($StoreLocation -eq "LocalMachine") {$true} else {$false}
        }
        '__file' {
            $PrivateKey.MachineContext = $false
        }
    }
    $PrivateKey.ExportPolicy = if ($Exportable) {1} else {0}
    $PrivateKey.Create()
#endregion

    # http://msdn.microsoft.com/en-us/library/aa377124(VS.85).aspx
    $Cert = New-Object -ComObject X509Enrollment.CX509CertificateRequestCertificate
    if ($PrivateKey.MachineContext) {
        $Cert.InitializeFromPrivateKey($MachineContext,$PrivateKey,"")
    } else {
        $Cert.InitializeFromPrivateKey($UserContext,$PrivateKey,"")
    }
    $Cert.Subject = $SubjectDN
    $Cert.Issuer = $Cert.Subject
    $Cert.NotBefore = $NotBefore
    $Cert.NotAfter = $NotAfter
    foreach ($item in $ExtensionsToAdd) {$Cert.X509Extensions.Add((Get-Variable -Name $item -ValueOnly))}
    if (![string]::IsNullOrEmpty($SerialNumber)) {
        if ($SerialNumber -match "[^0-9a-fA-F]") {throw "Invalid serial number specified."}
        if ($SerialNumber.Length % 2) {$SerialNumber = "0" + $SerialNumber}
        $Bytes = $SerialNumber -split "(.{2})" | ?{$_} | %{[Convert]::ToByte($_,16)}
        $ByteString = [Convert]::ToBase64String($Bytes)
        $Cert.SerialNumber.InvokeSet($ByteString,1)
    }
    if ($AllowSMIME) {$Cert.SmimeCapabilities = $true}
    $SigOID = New-Object -ComObject X509Enrollment.CObjectId
    $SigOID.InitializeFromValue(([Security.Cryptography.Oid]$SignatureAlgorithm).Value)
    $Cert.SignatureInformation.HashAlgorithm = $SigOID
    # completing certificate request template building
    $Cert.Encode()
    
    # interface: http://msdn.microsoft.com/en-us/library/aa377809(VS.85).aspx
    $Request = New-Object -ComObject X509Enrollment.CX509enrollment
    $Request.InitializeFromRequest($Cert)
    $Request.CertificateFriendlyName = $FriendlyName
    $endCert = $Request.CreateRequest($Base64)
    $Request.InstallResponse($AllowUntrustedCertificate,$endCert,$Base64,"")
    switch ($PSCmdlet.ParameterSetName) {
        '__file' {
            $PFXString = $Request.CreatePFX(
                [Runtime.InteropServices.Marshal]::PtrToStringAuto([Runtime.InteropServices.Marshal]::SecureStringToBSTR($Password)),
                $PFXExportEEOnly,
                $Base64
            )
            Set-Content -Path $Path -Value ([Convert]::FromBase64String($PFXString)) -Encoding Byte
        }
    }
}