Renew SSL Certs on Azure Application Gateway with Gitlab CI

Renewing SSL certificates on Azure Application Gateway is a regular toil for me. Whenever I research how to automate it, it felt like everyone uses some Azure tools that doesn’t fit to my liking. I don’t want to copy a year old Powershell script and paste it to an Azure automation account (Oh, I can’t even use an Azure Automation account because I don’t have the permission to register applications in my client’s Active Directory). I don’t want to provision a virtual server just to renew a certificate and no, I don’t want to use Azure Devops pipelines. I already have a CI tool that I like and even built some tools for it!

Today, I sat down and didn’t get up until work is done! I’ll explain my process so maybe someone luckier than me could find and use it.

We use Let’s Encrypt for all our SSL certificate needs (assuming the client doesn’t need PV or EV) and monitor certificates for all of our services. The services that run on on-premise data centers usually renew their certificates with good old cron but the services that runs on Azure doesn’t have a virtual machine that I can ssh into. They’re all run on several Azure App Service plans in Docker containers and behind Azure Traffic Manager and Azure Application Gateway. So whenever our monitoring system alarms me one or many of the certificates will expire soon I have to get a new certificate and upload it to Azure manually.

Manual process involves many steps:

  1. Create a new container using certbot image from Dockerhub.
  2. Attempt to get a new certificate using ‘certbot certonly –manual'
  3. Copy and paste validation code to a local file
  4. Upload file to a public container on Azure Blob Storage to let Let’s Encrypt servers validate my request
  5. Get the certificate and export it to pfx file using openssl
  6. Change old pfx file with new one in our terraform project
  7. Run terraform apply

It’s disgusting and also very error prone. What if I miss some unapplied change in the terraform plan (have you ever seen the diff of an Application Gateway change?). It’s also undocumented because whenever I try to document it, I always find myself in how-to-automate-this-shit rabbit hole.

I solved the problem using Gitlab CI pipelines. I wasn’t aware of certbot’s --manual-auth-hook option before. Once I saw it, rest came easy.

Here is the .gitlab-ci.yml:

  - letsencrypt

  stage: letsencrypt
    name: certbot/certbot:latest
    entrypoint: [""]
    - apk update
    - apk add gcc make python3-dev musl-dev openssl-dev
    - python -m venv venv
    - source venv/bin/activate
    - pip install --upgrade pip setuptools wheel
    - pip install azure-cli
    - az account set --subscription $AZ_SUBSCRIPTION_ID
    - certbot certonly --manual --preferred-challenges=http --manual-auth-hook letsencrypt/ -d $DOMAIN -m $CERTBOT_CONTACT_EMAIL --agree-tos --non-interactive --manual-public-ip-logging-ok
    - openssl pkcs12 -export -out $DOMAIN.pfx -inkey /etc/letsencrypt/live/$DOMAIN/privkey.pem -in /etc/letsencrypt/live/$DOMAIN/cert.pem -certfile /etc/letsencrypt/live/$DOMAIN/chain.pem -password env:PFX_PASSWORD
    - az network application-gateway ssl-cert update --resource-group $AZ_RESOURCE_GROUP_NAME --gateway-name $AZ_APP_GATEWAY_NAME --name $DOMAIN --cert-file $DOMAIN.pfx --cert-password $PFX_PASSWORD
    - web
    - api

The official certbot image uses Alpine as its base. So we need a bunch of packages to install Azure CLI. Then we get the new certificate. --manual-auth-hook do its job by passing validation string and token to our custom script.

The script is pretty straight forward:




az storage blob upload \
    --connection-string "$ACME_CHALLENGE_BLOB_CONNECTION_STRING" \
    --container-name "$ACME_CHALLENGE_BLOB_CONTAINER_NAME" \
    --file "$ACME_CHALLENGE_PATH" \

It just uploads the file to our public container. We already have URL maps in Gateway that points to this container for all listeners. Once certbot gives us the new certicate, openssl exports it to pfx file, and we change the old certificate with new one.

That’s it. Now I (and everyone) can just create a new pipeline using the Gitlab UI or my tool gitlabci.

Naturally, I prefer gitlabci:

$ gitlabci pipeline create group/project master -e

We can also create scheduled pipelines in the future. I need to make some changes to don’t make unnecessary updates to Gateway, though.

Now, that’s a solution that fits to my liking!