Key Vault Extension

Rotating server certificates in a large estate has always been a administration hassle, so let this key vault extension take the heavy lifting for both Azure and Azure Arc-enabled VMs.



Another nice extension is the Key Vault Extension. This will watch a certificate uploaded into a key vault and then pull it down to the server. Therefore you can rotate your certificates and allow the extensions to do all of the hard work.

On Windows server it will be installed into the selected certificate store.

For linux it is downloaded to a directory and you then install. (This last stage should be scripted.). As this is the slightly more complex version then we will work on the linux VMs for this one.

This is a guided lab rather than a challenge.

Access policy

For the Key Vault Extension to work, you need to ensure that the managed identity has access to get the secret. (Remember that certificates are uploaded into the certificate, key and secret areas of a key vault. The certificate part is just the public part, whereas the secret includes everything.)

If you don’t have Azure AD role to create a group then you can do individual assignments, but if you can create a group then this is arguably the more elegant approach.

Choose one of the following:

  1. Individual access policy per managed identity

    kv=$(az keyvault list --resource-group arc_pilot --query [0].name --output tsv)
    managedIdentityIds=$(az connectedmachine list --resource-group arc_pilot --query "[].identity.principalId" --output tsv)
    for id in $managedIdentityIds; do az keyvault set-policy --name $kv --secret-permissions list get --resource-group arc_pilot --object-id $id; done
  2. All managed identities in a security group

    kv=$(az keyvault list --resource-group arc_pilot --query [0].name --output tsv)
    groupId=$(az ad group create --display-name "Azure Arc-enabled servers" --mail-nickname arcservers --description "Managed identities for Azure Arc connected machines." --query objectId --output tsv)
    managedIdentityIds=$(az connectedmachine list --resource-group arc_pilot --query "[].identity.principalId" --output tsv)
    for id in $managedIdentityIds; do az ad group member add --group "Azure Arc-enabled servers" --member-id $id; done
    az ad group member list --group "Azure Arc-enabled servers" --query [].appId
    az keyvault set-policy --name $kv --secret-permissions list get --resource-group arc_pilot --object-id $groupId

Key Vault Extension

  1. Set the variables

    kv=$(az keyvault list --resource-group arc_pilot --query [0].name --output tsv)
  2. Create the Key Vault Extension

    az connectedmachine extension create --name KeyVaultForLinux --publisher Microsoft.Azure.KeyVault --type KeyVaultForLinux --machine-name ubuntu-03 --resource-group arc_pilot --settings "{\"secretsManagementSettings\":{\"pollingIntervalInS\":\"60\",\"observedCertificates\":[\"https://$$cert\"]},\"authenticationSettings\":{\"msiEndpoint\":\"http://localhost:40342/metadata/identity\"}}"

    The polling interval has been set to 60 seconds rather than the default 3600, or hourly.

    Note the quoted JSON string. These can be a syntactical nightmare, so the Creating quoted strings section at the end of this page has some useful hints.

  3. Repeat

    Repeat the last step for the other linux VMs.

Stretch targets (optional)

  1. Create the Key Vault Extension for the same certificate on the Windows servers

    Use the CA store.

  2. Update the certificate in the key vault


The extension will poll the key vault secret every minute and will download updates to /var/lib/waagent/Microsoft.Azure.KeyVault.Store/ in PEM format. This directory is only accessible to root.

  1. Once the extension creation has succeeded then you can check the folder.

    sudo ls /var/lib/waagent/Microsoft.Azure.KeyVault.Store/
    sudo cat /var/lib/waagent/Microsoft.Azure.KeyVault.Store/arc-pilot-dfc4852d.self-signed-cert

    Note the secret’s version is included in the full filename. The short form is a symbolic link to the latest of these files.

On Windows it will add to the specified certificateStoreName.

Certificate Installation

You would usually have a cronjob to check for new certificates in that location and then run these install steps. We’ll do it manually.

Set variables


Convert from PEM to DER

sudo openssl x509 -outform der -in $pem -out /usr/local/share/ca-certificates/self-signed-cert.crt

Update CA certificates

sudo update-ca-certificates

Success criteria

Screen share with your proctor to prove:

  • one of your linux VMs has the certificate

     openssl x509 -in  /usr/local/share/ca-certificates/self-signed-cert.crt -inform der -noout -text
  • one of your Windows VMs has the certificate in the store (stretch)


The extension manager writes out to /var/lib/GuestConfig/ext_mgr_logs.

The extension agents write out to the /var/lib/waagent/ area on linux.

We’ll see the Windows equivalents for the Custom Script Extension in the next lab.

Creating JSON strings

This section is purely for info.

If you are having difficulty creating JSON strings then first create a JSON file in vscode to check it is syntactically valid.


  "secretsManagementSettings": {
    "pollingIntervalInS": "3600",
    "certificateStoreLocation": "/var/lib/waagent/Microsoft.Azure.KeyVault.Store/",
    "certificateStoreName": "ignored",
    "observedCertificates": [
  "authenticationSettings": {
    "msiEndpoint": "http://localhost:40342/metadata/identity"

The default certificateStoreLocation has been included for completeness. For Windows just specify the machine name.

Quoted string

If your JSON includes bash variables then you can convert it to a quoted JSON string using jq.

jq @json settings.json



Single quoted string

If all of the values are hardcoded then you can just minify it and then enclose in single quotes. This will be a little more readable.

jq -Mc . settings.json



Surround with single quotes.


JSON file

If the file will be present then keep it simple and just specify the filename.

az connectedmachine extension create --name KeyVaultForLinux --publisher Microsoft.Azure.KeyVault --type KeyVaultForLinux --machine-name ubuntu-02 --resource-group arc_pilot --settings settings.json



Next we will use the Custom Script Extension to run PowerShell and bash scripts on the connected servers.

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