Certificate Update

Certificate Update


When deploying a Chocolatey for Business (C4B) Azure Environment, you are asked to supply an SSL certificate. This page shows you how to update that certificate when the original is expiring or has been regenerated for any other reason.

To perform this operation you will need to have permissions sufficient to edit Access Policies on the environment’s Azure Key Vault.

Please note that it can take some time for all of the components in your C4B Azure Environment to reflect the new certificate.

For portions of this document using PowerShell, we assume you have installed a recent version of the Az modules (easily available by running choco install az.powershell in an elevated prompt), and have logged in to your account using Connect-AzAccount. You can also set a variable, $ResourceGroupName, to the name of the resource group you deployed the Chocolatey for Business Azure Environment to as we will use this with the PowerShell code snippets below.

Access Policies

Similar to the Access Policies configuration needed to access the usernames and passwords for the services running in your C4B Azure Environment, you will need to configure access to manage the SSL certificate.

You can adjust the Access Policies using the Azure Portal or PowerShell.

Azure Portal

  1. Navigate to the Resource Group that contains your C4B Azure Environment.

  2. Select the Key vault.

    Key vault resource

  3. Under Settings on the left of the blade, select Access Policies.

  4. Click + Add Access Policy.

    Vault Access Policies

  5. Select, at a minimum, Certificate Permissions: Get, List, Import, and Update (You can use a Template such as Certificate Management).

    Secret Permissions

  6. Under Select Principal, click None Selected and find your current user, and select it.

  7. Click Add.

    Add Principal

  8. Back on the Access Policies blade, hit Save and wait for the operation to complete.


if (-not $ResourceGroupName) {$ResourceGroupName = Read-Host 'Enter the ResourceGroupName'}
$CurrentUser = (Get-AzContext).Account.Id

# Grant access to the KeyVault, if missing
$KeyVault = Get-AzKeyVault -ResourceGroupName $ResourceGroupName | ForEach-Object {Get-AzKeyVault -VaultName $_.VaultName}
$CertPermissions = $KeyVault.AccessPolicies.Where{$_.DisplayName -like "*$CurrentUser*"}.PermissionsToCertificates
if ($CertPermissions -notcontains 'Get' -or $CertPermissions -notcontains 'List' -or $CertPermissions -notcontains 'Update' -or $CertPermissions -notcontains 'Import') {
    $NewCertPermissions = $CertPermissions + @('Get', 'List', 'Update', 'Import') | Select-Object -Unique
    Set-AzKeyVaultAccessPolicy -VaultName $KeyVault.VaultName -UserPrincipalName $CurrentUser -PermissionsToCertificates $NewCertPermissions

Updating the Azure Key Vault

The certificate used by most of the C4B Azure Environment is stored in the provided Azure Key Vault under the name C4B-Azure-Certificate. To update the certificate used by the environment, you create a new version of this certificate.


Please note that the new certificate must meet the same requirements as the original did during the initial deployment. The certificate:

  • Needs to be in the PFX format.
  • Needs to include an exportable Private Key.
  • Must have a password.

You can upload a new version of the certificate using the Azure Portal or PowerShell.

Azure Portal

  1. Within the Key Vault, under Settings on the left of the blade, select Certificates.

  2. Select the certificate named C4B-Azure-Certificate.

    Vault Certificates

  3. Click + New Version.

    Vault Certificates New Version

  4. Change the Method of Certificate Creation to Import.

  5. Upload your certificate PFX file, and provide the password needed to import it.

    Vault Import Certificates

  6. Click Create.

  7. The new certificate will now be listed as the CURRENT VERSION and any previous certificates will be listed under OLDER VERSIONS.

    Vault Certificate Version List


This script prompts you for the name of the Resource Group that contains your C4B Azure Environment and then opens a dialog box to select your new certificate.

if (-not $ResourceGroupName) {$ResourceGroupName = Read-Host 'Enter the ResourceGroupName'}
$KeyVault = Get-AzKeyVault -ResourceGroupName $ResourceGroupName | ForEach-Object {Get-AzKeyVault -VaultName $_.VaultName}

$null = [System.Reflection.Assembly]::LoadWithPartialName("System.Windows.Forms")
$FileBrowser = New-Object System.Windows.Forms.OpenFileDialog -Property @{
    Title  = 'Select Chocolatey for Business Azure Environment Certificate'
    Filter = 'Certificate (*.pfx)|*.pfx'
$null = $FileBrowser.ShowDialog()

$CertImport = @{
    VaultName = $KeyVault.VaultName
    Name      = 'C4B-Azure-Certificate'
    FilePath  = $FileBrowser.FileName
$null = Import-AzKeyVaultCertificate @CertImport -Password (Read-Host "Enter the certificate import password" -AsSecureString)

Updating the Application Gateway

The Application Gateway provided with your C4B Azure Environment needs to be updated manually, as it is not able to reference the Azure Key Vault.

Azure Portal


In addition to the certificate in a PFX format that was used in the previous section, you will need a copy of the certificate in CER format.

You can convert your existing certificate using OpenSSL (easily installed by running choco install openssl.light):

openssl pkcs12 -in certificate.pfx -out certificate.cer -nokeys -clcerts

You will need to edit the resulting file to remove all of the text above the -----BEGIN CERTIFICATE----- line.

  1. Navigate to the Resource Group the contains your C4B Azure Environment.

  2. Select the Application gateway.

    Application Gateway resource

  3. Under Settings on the left of the blade, select Backend settings.

  4. Select CCMService.

    Application Gateway backend settings

  5. On the Add Backend settings blade, click + Add certificate.

    Backend setting add certificate

  6. Ensure Create new is selected and browse to the .cer version of your certificate.

  7. Provide a descriptive Cert name that is different to the existing certificate. The initial certificate is called CCMCert.

  8. Click + Add certificate.

    Add backend certificate

  9. Click the ... (three dots) to the right of the previous certificate and choose Delete.

  10. Click Save.

    Save new backend certificate

  11. Under Settings on the left of the blade, select Listeners.

  12. Select CCM.

    Application Gateway listeners settings

  13. Ensure SslCertificate is the selected certificate.

  14. Check Renew or edit selected certificate.

  15. Browse to select the .pfx version of your certificate.

  16. Enter the Password required to import the certificate.

  17. Click Save.

    Application Gateway listeners cert update

  18. It can take some time for the Application Gateway to update. When it has finished you will be able check that the new certificate is being served by visiting on the C4B Azure Environment services.


Please note that until the Set-AzApplicationGateway command is run, the Application Gateway will not be updated. The update can take up to 30 minutes, but the command should return immediately.

if (-not $ResourceGroupName) {$ResourceGroupName = Read-Host 'Enter the ResourceGroupName'}
$ApplicationGateway = Get-AzApplicationGateway -ResourceGroupName $ResourceGroupName

$null = [System.Reflection.Assembly]::LoadWithPartialName("System.Windows.Forms")
if (-not $FileBrowser.FileName) {
    $FileBrowser = New-Object System.Windows.Forms.OpenFileDialog -Property @{
        Title  = 'Select Chocolatey for Business Azure Environment Certificate'
        Filter = 'Certificate (*.pfx)|*.pfx'
    $null = $FileBrowser.ShowDialog()

$CertificateDetails = @{
    Name               = "SslCertificate"
    CertificateFile    = $FileBrowser.FileName
    Password           = Read-Host "Enter the certificate import password" -AsSecureString

# Set the listener SSL certificate
$ApplicationGateway = Set-AzApplicationGatewaySslCertificate -ApplicationGateway $ApplicationGateway @CertificateDetails

# Convert the certificate to a CER format
$Cert = [System.Security.Cryptography.X509Certificates.X509Certificate2]::new(
    32  # EphemeralKeySet
[IO.File]::WriteAllBytes(($TemporaryCerPath = New-TemporaryFile), $Cert.Export("Cert"))

# Set the authentication certificate for the CCM service
$ApplicationGateway = Set-AzApplicationGatewayAuthenticationCertificate -ApplicationGateway $ApplicationGateway -Name "CCMCert" -CertificateFile $TemporaryCerPath

# "Save" the new settings to the Application Gateway
$null = Set-AzApplicationGateway -ApplicationGateway $ApplicationGateway

# Clean up the temporary CER
Remove-Item $TemporaryCerPath


I’ve uploaded a new certificate, why hasn’t it been applied?

Some components of the C4B Azure Environment need to select between multiple versions of a certificate when determining if an update is required.

The determining factor is the NotBefore date on the certificate. The latest date is considered to belong to the newest certificate.

You can check the NotBefore property of a pfx file using PowerShell:

$CertificatePath = Read-Host 'Enter the path to the certificate file'
Get-PfxCertificate -FilePath $CertificatePath | Select-Object NotBefore