Provisioning windows box with Chef-provisioning on azure from a mac

After spending about half a day trying to get vagrant-azure to work it became very clear, that as of this writing the driver is just not mature enough. It works pretty good for Ubuntu/Linux but the moment you try to provision windows boxes, it sets your laptop on fire.

Instead of wasting any more time on it, I decided to give v1 and v2 provisioning drivers a chance, followed by Test Kitchen. IIRC they all use different drivers, and while all are pretty solid at provisioning Linux boxes, support for WinRM is very spotty.

Authentication:

First challenge is to authenticate successfully via provisioning driver. While Vagrant accepts subscription id and path to .pem as parameters, provisioning needs a azureProfile.json.

To get that file generated, I installed azure-cli via brew `brew cask install azure-cli`

Next, import azure creds with `azure account import ../../Projects/Azure/myazure.publishsettings`
This command will generate the missing azureProfile.json in ~/.azure

Next, validate it works with `azure account list`

Chef-Provisioning piece:

Get a name of the box (ami) you'll be using: `azure vm image list | grep -i Win2012`

Next, hack up the simplest recipe that'll spin up a box:

`knife cookbook create azure_old`
content of recipe/default.rb:

require 'chef/provisioning/azure_driver'
with_driver 'azure'
machine_options = {
    :bootstrap_options => {
      :cloud_service_name => 'alexvinyar', #required
      :storage_account_name => 'alexvinyar', #required
      :vm_size => "Standard_D1", #required
      :location => 'West US', #required
      :tcp_endpoints => '80:80' #optional
    },
    :image_id => 'b39f27a8b8c64d52b05eac6a62ebad85__Ubuntu-14_04_2-LTS-amd64-server-20150706-en-us-30GB', #required
    # :image_id => 'a699494373c04fc0bc8f2bb1389d6106__Windows-Server-2012-R2-20150916-en.us-127GB.vhd', #next step
    # Until SSH keys are supported (soon)
    :password => 'Not**RealPass' #required
}
machine 'toad' do
  machine_options machine_options
  ohai_hints 'azure' => { 'a22' => 'b33' }
end

Finally, run chef-zero (chef client in local mode): `chef-client -z -r azure_old`

If the above recipe fails, dont fail. Check the output, and see if it gets past the authentication piece. If it does, it's just a matter of getting chef-provisioning syntax correct.

Once the run finishes (Azure is slow) connect to the box with `ssh root@12.23.34.45` for centos or ubuntu@ip for ubuntu boxes.

Now the Windows piece

With the `azure vm image list | grep -i Win2012` command I got a list of boxes, and once the test run with ubuntu succeeds, I move on to Windows.

This is where I took a break and had a beer. But I published this post anyway because I'll finish it eventually.

Useful links:
http://azure.microsoft.com/en-us/documentation/articles/xplat-cli/
http://brew.sh/
https://unindented.org/articles/provision-azure-boxes-with-vagrant/