Store a private key in Azure Key Vault for use in a Logic App

Today, I found myself in need of an automated SFTP connection that would reach out to one of our partners, download a file, and then dump it in to a Data Lake for further processing. This meant that I would need to store a private in Azure Key Vault for use in a Logic App. While this was mainly a straightforward process, there was a small hiccup that we encountered and wanted to pass along.

First, we went ahead and generated a public/private key pair using:

ssh-keygen -t rsa -b 4096

where rsa is the algorithm and 4096 is the length of the key in bits. We avoided the ec25519 and ecdsa algorithms as our partner does not support elliptic-curve cryptography. As this command was run on a Mac laptop which already has it’s own ~/.ssh/id_rsa[.pub] key pair, we chose a new filename and location /tmp/sftp to temporarily store this new pair.

The problem arose when we tried to insert the private key data into Key Vault as a secret: the Azure portal does not support multi-line secret entry, resulting in a non-standard and ultimately broken key entry.

The solution was to use the Azure CLI to upload the contents of the private key by doing:

az keyvault secret set --vault-name sftp-keyvault -n private-key -f '/tmp/sftp'

This uploaded the file correctly to the secret titled private-key, which means that we can now add a Key Vault action in our Logic App to pull the secret, without having to leave the key in plain view, and then use it as the data source for the private key field in SFTP - Copy File action.

As an aside, we also created a new secret called public-key and uploaded a copy of just so that 6 months from now if we need to recall a copy of it to send to another partner, it’s there for us to grab.

Integrating Azure Kubernetes Service and Azure Container Registry

At our office, we’ve been using Docker containers deployed to Azure App Service for Containers for all of our microservices, but after a few incidents in the past couple of weeks, we’ve decided to look into managing our own Kubernetes cluster, but we quickly found out that integrating Azure Kubernetes Service and Azure Container Registry took a little bit of tweaking.

The main issue is that having AKS authenticate against ACR requires setting up a service principal and then instructing AKS to use that SP. It’s not hard to set up, but there are a few steps and I wanted to bring them all to one place to make things easier for you in the future.

I’m going to describe this process from the perspective of someone who already has a container registry and Kubernetes cluster stood up and just need to tie the two together. There are plenty of tutorials on how to stand each of those services up themselves and so I’ll leave it as an exercise for the reader to get to this point.

You should also be aware that the AKS cluster and the ACR must be in the same subscription for this process to work.

Step 1: Create the service principal using the following BASH script


echo -n "Ensure you are logged into Azure CLI before continuing and then press [ENTER]"
echo -n ""
echo -n "Enter the name of the container registry (*without* the and press [ENTER]: "
echo -n "Enter the name of the service prinicpal you would like to create (e.g. test-sp-dev) and press [ENTER]: "

# Populate the ACR login server and resource id.

ACR_LOGIN_SERVER=$(az acr show --name $ACR_NAME --query loginServer --output tsv)
ACR_REGISTRY_ID=$(az acr show --name $ACR_NAME --query id --output tsv)

# Create acrpull role assignment with a scope of the ACR resource.

SP_PASSWD=$(az ad sp create-for-rbac --name http://$SERVICE_PRINCIPAL_NAME --role acrpull --scopes $ACR_REGISTRY_ID --query password --output tsv)

# Get the service principal client id.

CLIENT_ID=$(az ad sp show --id http://$SERVICE_PRINCIPAL_NAME --query appId --output tsv)

# Output used when creating Kubernetes secret.

echo "Service principal ID: $CLIENT_ID"
echo "Service principal password: $SP_PASSWD"

You will want to make note of this ID and password combination for future troubleshooting as well as in the instances where you cannot proceed through step 4 of this post in the same terminal instance.

Step 2: Install the aks cli from az cli

az aks install-cli

NOTE: You may need to run this command using sudo if you are on a Linux/MacOS/BSD computer

Step 3: Authenticate to your AKS cluster

Let’s assume that I have a Kubernetes cluster called nexxai-k8s-dev in a resource group also called nexxai-k8s-dev. I would run:

az aks get-credentials --resource-group nexxai-k8s-dev --name nexxai-k8s-dev
kubectl create clusterrolebinding kubernetes-dashboard --clusterrole=cluster-admin --serviceaccount=kube-system:kubernetes-dashboard

NOTE: The kubectl command just solves a permissions issue that appears if you try to access the Kubernetes dashboard using az aks browse --resource-group nexxai-k8s-dev --name nexxai-k8s-dev. If you plan on doing things only through the CLI, I’m not sure if this step is required and you may be able to skip it.

Step 4: Tell Kubernetes to use that Service Principal

Let’s assume that I have a container registry called nexxai-acr-dev and I want to name the secret acr-auth. I would run:

kubectl create secret docker-registry acr-auth --docker-server --docker-username $CLIENT_ID --docker-password $SP_PASSWD --docker-email [email protected]

This command assumes you are working in the same terminal as when you executed the BASH script in step 1, and uses their variables. If you are not working in the same terminal session as in step 1, simply substitute $CLIENT_ID and $SP_PASSWD with their actual values.

Step 5: Profit!

At this point your new Kubernetes cluster is ready to talk to your container registry!

Now all you need to remember is that when you go to create a deployment, you need to provide the entire ACR address (including the part of the domain) for the image setting, and you’ll need to define the imagePullSecrets block and set its name property to acr-auth in your YAML file like this:

apiVersion: apps/v1
kind: Deployment
name: demo-app-dev-deploy
app: demo-app
replicas: 3
app: demo-app
app: demo-app
- name: demo-app
- containerPort: 4000
- name: acr-auth

And finally, by exposing the deployment using the command below, you’ll have a fully functional application that lives in Azure Kubernetes Service and uses Azure Container Registry to host its code.

kubectl expose deployment demo-app-dev-deploy --type=LoadBalancer --name=demo-app-dev


How to import a publicly-issued certificate into Azure Key Vault

Today, after spending several hours swearing and researching how to import a publicly-issued certificate into Azure Key Vault, I thought I’d share the entire process of how we did it from start to finish so that you can save yourself a bunch of time and get back to working on fun stuff, like spamming your co-workers with Cat Facts. We learned a bunch about the different encoding formats of certificates and some of their restrictions, both within Azure Key Vault as well as with the certificate types themselves. Let’s get started!

Initially, we created an elliptic curve-derived (EC) private key (using elliptic curve prime256v1), and a CSR by doing:

openssl ecparam -out privatekey.key -name prime256v1 -genkey
openssl req -new -key privatekey.key -out request.csr -sha256

making sure to not include an email address or password. I am not actually clear on what the technical reasoning behind this is, but I saw it noted on several sites.

We submitted the CSR to our certificate authority (CA) and shortly thereafter got back a signed PEM file.

We next needed to create a single PFX/PKCS12-formatted, password-protected certificate, so we grabbed our signed certificate (ServerCertificate.crt) and our CA’s intermediate certificate chain (Chain.crt) and then did:

openssl pkcs12 -export -inkey privatekey.key -in ServerCertificate.crt -certfile Chain.crt -out Certificate.pfx

But when we went to import it into the Key Vault with the correct password, it threw a general “We don’t like this certificate” error. The first thing we did was check out the provided link and saw that we could import PEM-formatted certificates directly. I didn’t remember this being the case in the past, so maybe this is a new feature?

No problem. We concatenated the certificate and key files into a single, large text file (echo ServerCertificate.crt >> concat.crt ; echo privatekey.key >> concat.crt) which would create a file called concat.crt which itself would consist of the

-----------BEGIN CERTIFICATE-----------
-----------END CERTIFICATE-----------

section from the ServerCertificate.crt file as well as the




sections from the privatekey.key file.

We went to upload concat.crt to the Key Vault and again were given the same error as before however after re-reading the document, we were disappointed when we saw this quote:

We currently don’t support EC keys in PEM format.

Section: Formats of Import we support

It surprises me that Microsoft does not support elliptic curve-based keys in PEM format. I am not aware of any technical limitation on the part of the certificate so this seems very much like a Microsoft-specfic thing, however if anyone is able to provide insight into this, I’d love to hear it.

OK, we’ll generate an 2048-bit RSA-derived key and CSR, and then try again.

openssl genrsa -des3 -out rsaprivate.key 2048
openssl req -new -key rsaprivate.key -out RSA.csr

We uploaded the CSR to the CA as a re-key request, and waited.

When the certificate was finally issued (as cert.pem), we could now take the final steps to prepare it for upload to the Key Vault. We concatenated the key and certificate together (echo rsaprivate.key >> rsacert.crt ; echo cert.pem >> rsacert.crt) and went to upload it to the Key Vault.

And yet again, it failed. After a bunch of researching on security blogs and StackOverflow, it turns out that the default output format of the private key is PKCS1, and Key Vault expects it to be in PKCS8 format. So now time to convert it.

openssl pkcs8 -topk8 -inform PEM -outform PEM -nocrypt -in rsaprivate.key -out rsaprivate8.key

Finally, we re-concatenated the rsaprivate8.key and cert.pem files into a single rsacert8.crt file (echo rsaprivate8.key >> rsacert8.crt ; echo cert.pem >> rsacert8.crt) which we could import into Key Vault.

It worked!

We now have our SSL certificate in our HSM-backed Azure Key Vault that we can apply to our various web properties without having to store the actual certificate files anywhere, which makes our auditors very happy.

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