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Gerar certificado autoassinado com o assinante de CA raiz


A solução definitiva no meu caso, evitando makecert e openssl, foi usar Powershell e BouncyCastle. Fiz um fork do repositório PSBouncyCastle de PSBouncyCastle por RLipscombe e empurrado 1.8.1 Bouncy Castle. Minha versão bifurcada é a que eu usei para o script, a bifurcação reside em Forked:PSBouncyCastle.New .

Em seguida, usei StackOverflow:C# Generate Certificates on the Fly como inspiração para escrever o seguinte powershell abaixo, Vou adicionar isso ao meu GitHub e comentar, e vou corrigir isso assim que o fizer :
Import-Module -Name PSBouncyCastle.New

function New-SelfSignedCertificate {
  [CmdletBinding()]
  param (
    [string]$SubjectName,
    [string]$FriendlyName = "New Certificate",
    [object]$Issuer,
    [bool]$IsCA = $false,
    [int]$KeyStrength = 2048,
    [int]$ValidYears = 2,
    [hashtable]$EKU = @{}
  )

  # Needed generators
  $random = New-SecureRandom
  $certificateGenerator = New-CertificateGenerator

  if($Issuer -ne $null -and $Issuer.HasPrivateKey -eq $true)
  {
    $IssuerName = $Issuer.IssuerName.Name
    $IssuerPrivateKey = $Issuer.PrivateKey
  }
  # Create and set a random certificate serial number
  $serial = New-SerialNumber -Random $random
  $certificateGenerator.SetSerialNumber($serial)

  # The signature algorithm
  $certificateGenerator.SetSignatureAlgorithm('SHA256WithRSA')

  # Basic Constraints - certificate is allowed to be used as intermediate.
  # Powershell requires either a $null or reassignment or it will return this from the function
  $certificateGenerator = Add-BasicConstraints -isCertificateAuthority $IsCA -certificateGenerator $certificateGenerator

  # Key Usage
  if($EKU.Count -gt 0) 
  {
    $certificateGenerator = $certificateGenerator | Add-ExtendedKeyUsage @EKU
  }
  # Create and set the Issuer and Subject name
  $subjectDN = New-X509Name -Name ($SubjectName)
  if($Issuer -ne $null) {
    $IssuerDN = New-X509Name -Name ($IssuerName)
  }
  else 
  {
    $IssuerDN = New-X509Name -Name ($SubjectName)
  }  
  $certificateGenerator.SetSubjectDN($subjectDN)
  $certificateGenerator.SetIssuerDN($IssuerDN)

  # Authority Key and Subject Identifier
  if($Issuer -ne $null)
  {
    $IssuerKeyPair = ConvertTo-BouncyCastleKeyPair -PrivateKey $IssuerPrivateKey
    $IssuerSerial = [Org.BouncyCastle.Math.BigInteger]$Issuer.GetSerialNumber()
    $authorityKeyIdentifier = New-AuthorityKeyIdentifier -name $Issuer.IssuerName.Name -publicKey $IssuerKeyPair.Public -serialNumber $IssuerSerial
    $certificateGenerator = Add-AuthorityKeyIdentifier -certificateGenerator $certificateGenerator -authorityKeyIdentifier $authorityKeyIdentifier
  }

  # Validity range of the certificate
  [DateTime]$notBefore = (Get-Date).AddDays(-1)
  if($ValidYears -gt 0) {
    [DateTime]$notAfter = $notBefore.AddYears($ValidYears)
  }
  $certificateGenerator.SetNotBefore($notBefore)
  $certificateGenerator.SetNotAfter($notAfter)


  # Subject public key ~and private
  $subjectKeyPair = New-KeyPair -Strength $keyStrength -Random $random
  if($IssuerPrivateKey -ne $null)
  {
    $IssuerKeyPair = [Org.BouncyCastle.Security.DotNetUtilities]::GetKeyPair($IssuerPrivateKey)
  }
  else 
  {
    $IssuerKeyPair = $subjectKeyPair
  }
  $certificateGenerator.SetPublicKey($subjectKeyPair.Public)

  # Create the Certificate
  $IssuerKeyPair = $subjectKeyPair
  $certificate = $certificateGenerator.Generate($IssuerKeyPair.Private, $random)
  # At this point you have the certificate and need to convert it and export, I return the private key for signing the next cert
  $pfxCertificate = ConvertFrom-BouncyCastleCertificate -certificate $certificate -subjectKeyPair $subjectKeyPair -friendlyName $FriendlyName
  return $pfxCertificate
}

Alguns exemplos de uso para este powershell seriam:

Gerar uma CA raiz
$TestRootCA = New-SelfSignedCertificate -subjectName "CN=TestRootCA" -IsCA $true
Export-Certificate -Certificate $test -OutputFile "TestRootCA.pfx" -X509ContentType Pfx

Gerar um padrão autoassinado
$TestSS = New-SelfSignedCertificate -subjectName "CN=TestLocal"
Export-Certificate -Certificate $TestSS -OutputFile "TestLocal.pfx" -X509ContentType Pfx

Gere um certificado, assinando com um certificado raiz
$TestRootCA = New-SelfSignedCertificate -subjectName "CN=TestRootCA" -IsCA $true
$TestSigned = New-SelfSignedCertificate -subjectName "CN=TestSignedByRoot" -issuer $TestRootCA

Export-Certificate -Certificate $test -OutputFile "TestRootCA.pfx" -X509ContentType Pfx
Export-Certificate -Certificate $test -OutputFile "TestRootCA.pfx" -X509ContentType Pfx

Gerar um auto-assinado com uso específico
$TestServerCert = New-SelfSignedCertificate -subjectName "CN=TestServerCert" -EKU @{ "ServerAuthentication" = $true }

Observe que o parâmetro -EKU aceita via splatting, ele faz isso para garantir que qualquer coisa adicionada a Add-ExtendedKeyUsage seja passada de forma válida. Ele aceita os seguintes usos de certificado:
  • Assinatura Digital
  • Não repúdio
  • KeyEncipherment
  • Encriptação de dados
  • Acordo de Chave
  • KeyCertSign
  • CrlSign
  • Somente criptografia
  • Somente Decifrar

Isso atende à minha necessidade e parece funcionar em todas as plataformas Windows que estamos usando para ambientes dinâmicos.