Deploying an Azure App Service from scratch, including DNS and TLS

As many of you have probably gathered, over the past few weeks, I’ve been working on building a process for deploying an Azure App Service from scratch, including DNS and TLS in a single Terraform module.

Today, I write this post with success in my heart, and at the bottom, I provide copies of the necessary files for your own usage.

One of the biggest hurdles I faced was trying to integrate Cloudflare’s CDN services with Azure’s Custom Domain verification. Typically, I’ll rely on the options available in the GUI as the inclusive list of “things I can do” so up until now, if we wanted to stand up a multi-region App Service, we had to do the following:

  1. Build and deploy the App Service, using the hostname for HTTPS for each region (R1 and R2)

    e.g. (R1), (R2)
  2. Create the CNAME record for the service at Cloudflare pointing at R1, turning off proxying (orange cloud off)

    e.g. ->
  3. Add the Custom Domain on R1, using the CNAME verification method
  4. Once the hostname is verified, go back to Cloudflare and update the CNAME record for the service to point to R2

    e.g. ->
  5. Add the Custom Domain on R2, using the CNAME verification method
  6. Once the hostname is verified, go back to Cloudflare and update the CNAME record for the service to point to the Traffic Manager, and also turn on proxying (orange cloud on)

While this eventually accomplishes the task, the failure mode it introduces is that if you ever want to add a third (or fourth or fifth…) region, you temporarily have to not only direct all traffic to your brand new single instance momentarily to verify the domain, but you also have to turn off proxying, exposing the fact that you are using Azure (bad OPSEC).

After doing some digging however, I came across a Microsoft document that explains that there is a way to add a TXT record which you can use to verify ownership of the domain without a bunch of messing around with the original record you’re dealing with.

This is great because we can just add new awverify records for each region and Azure will trust we own them, but Terraform introduces a new wrinkle in that it creates the record at Cloudflare so fast that Cloudflare’s infrastructure often doesn’t have time to replicate the new entry across their fleet before you attempt the verification, which means that the lookup will fail and Terraform will die.

To get around this, we added a null_resource that just executes a 30 second sleep to allow time for the record to propagate through Cloudflare’s network before attempting the lookup.

I’ve put together a copy of our Terraform modules for your perusal and usage:

Using this module will allow you to easily deploy all of your micro-services in a Highly Available configuration by utilizing multiple regions.

Generate Terraform files for existing resources

You may find yourself in a position where a resource already exists in your cloud environment but was created in the respective provider’s GUI rather than in Terraform. You may feel a bit overwhelmed at first, but there are a few ways to generate Terraform files for existing resources, and we’re going to talk about the various ways today. This is also not an exhaustive list; if you have any other suggestions, please leave a comment and I’ll be sure to update this post.

Method 1 – Manual

Be warned, the manual method takes a little more time, but is not restricted to certain resource types. I prefer this method because it means that you’ll be able to see every setting that is already set on your resource with your own two eyes, which is good for sanity checking.

First, you’re going to want to create a .tf file with just the outline of the resource type you’re trying to import or generate.

For example, if I wanted to create the Terraform for a resource group called example-resource-group that had several tags attached to it, I would do:

resource "azurerm_resource_group" "example-resource-group" {

and then save it.

Next, I would go to the Azure GUI, find and open the resource group, and then open the ‘Properties’ section from the blade.

I would look for the Resource ID, for example /subscriptions/54ba8d50-7332-4f23-88fe-f88221f75bb3/resourceGroups/example-resource-group and copy it.

I would then open up a command prompt / terminal and import the state by running: terraform import azurerm_resource_group.example-resource-group /subscriptions/54ba8d50-7332-4f23-88fe-f88221f75bb3/resourceGroups/example-resource-group

Finally, and this is the crucial part, I would immediately run terraform plan. There may be required fields that you will need to fill out before this comamnd works, but in general, this will compare the existing state that you just imported to the blank resource in the .tf file, and show you all of the differences which you can then copy into your new Terraform file, and be confident that you have imported all of the settings.


# azurerm_resource_group.example-resource-group will be updated in-place
   ~ resource "azurerm_resource_group" "example-resource-group" {
         id       = "/subscriptions/54ba8d50-7332-4f23-88fe-f88221f75bb3/resourceGroups/example-resource-group"
         location = "centralus"
         name     = "example-resource-group"
       ~ tags     = {
           ~ "environment" = "dev" -> null
           ~ "owner"       = "example.person" -> null
           ~ "product"     = "internal" -> null

A shortcut I’ve found is to just copy the entire resource section, and then replace all of the tildes (~) with spaces, and then find and remove all instances of -> null.

Method 2 – Az2tf (Azure only)

Andy Thomas (Microsoft employee) put together a tool called Az2tf which iterates over your entire subscription, and generates .tf files for most of the common types of resources, and he’s adding more all the time. Requesting a specific resource type is as simple as opening an issue and explaining which resource is missing. In my experience, he’s responded within a few hours with a solution.

Method 3 – Terraforming (AWS only)

Daisuke Fujita put together a tool called Terraforming that with a little bit of scripting can generate Terraform files for all of your AWS resources.

Method 4 – cf-terraforming (Cloudflare only)

Cloudflare put together a fantastic tool called cf-terraforming which rips through your Cloudflare tenant and generates .tf files for everything Cloudflare related. The great thing about cf-terraforming is that because it’s written by the vendor of the original product, they treat it as a first class citizen and keep it very up-to-date with any new resources they themselves add to their product. I wish all vendors would do this.

To sum things up, there are plenty of ways to generate Terraform files for existing resources. Some are more time consuming than others, but they all have the goal of making your environment less brittle and your processes more repeatable, which will save time, money, and most importantly stress, when an inevitable incident takes place.

Do you know of any other tools for these or other providers that can assist in bringing previously unmanaged resources under Terraform management? Leave a comment and we’ll add them to this page as soon as possible!

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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