• Converting a Vagrant VirtualBox .box file to Hyper-V

    I maintain quite a number of Chocolatey packages, and sometimes I need to test a new package out, or resolve an issue that has been reported with an updated version of a package. If it is for software that I use regularly, I’ll likely do the testing directly on my own machine. But if otherwise a virtual machine makes much more sense, as I can dispose of it once I’m done.

    Vagrant logo

    Chocolatey even provides a semi-automated way to do this using the HashiCorp tool Vagrant. They have a pre-built Windows image that is identical to the one they use for their own package verification process. Have a look at the https://github.com/chocolatey-community/chocolatey-test-environment repo to find out more.

    One issue I’ve encountered relates to the recent upgrading of the image to version 3.0.0, which is now is based on Windows Server 2019. The previous image version (2.0.0) was built using 2012R2. Unfortunately, for some reason while the older image was provided in both VirtualBox and Hyper-V formats, the 3.0.0 image currently only has VirtualBox support. Given the choice, I’d prefer to stick with Hyper-V (rather than having to install another hypervisor on my machine). The problem is if I follow the instructions and use the default Vagrantfile from the Chocolatey test environment repository, if I only have Hyper-V installed, it will download the older 2.0.0 image. How can I use the newer one? What follows are the steps I used to create a Hyper-V compatible box file from the VirtualBox one.

    First off, download the 3.0.0 image that targets VirtualBox. I don’t have VirtualBox installed, but you can still tell Vagrant to download that format by providing the --provider parameter. e.g.

    vagrant box add chocolatey/test-environment --provider VirtualBox

    You’ll see the following output (it may take a few minutes as like most Windows VM images, it is quite large)

    ==> box: Loading metadata for box 'chocolatey/test-environment'
        box: URL: https://vagrantcloud.com/chocolatey/test-environment
    ==> box: Adding box 'chocolatey/test-environment' (v3.0.0) for provider: VirtualBox
        box: Downloading: https://vagrantcloud.com/chocolatey/boxes/test-environment/versions/3.0.0/providers/VirtualBox/unknown/vagrant.box
        box: Calculating and comparing box checksum...
    ==> box: Successfully added box 'chocolatey/test-environment' (v3.0.0) for 'VirtualBox'!

    The files for this image are saved under the vagrant.d directory in your user profile. eg. for me they’re in


    In this directory, you can see the following files:

    Mode                LastWriteTime         Length Name
    ----                -------------         ------ ----
    -a---        15/10/2023  12:38 PM           9047   box.ovf
    -a---        15/10/2023  12:38 PM     7993072640 󰋊  chocolatey-test-environment-disk001.vmdk
    -a---        15/10/2023  12:38 PM             26   metadata.json
    -a---        15/10/2023  12:38 PM           3700   Vagrantfile

    Ah haa. A .VMDK file! Now we need to convert this to a VHD. There’s a few different ways to do this. The most reliable I’ve found is the StarWind V2V Converter tool

    StarWind V2V Conversion Wizard - Select source image location, local file

    StarWind V2V Conversion Wizard - Select source image

    StarWind V2V Conversion Wizard - Select destination image, local file

    StarWind V2V Conversion Wizard - Select destination image format, VHD/VHDX

    StarWind V2V Conversion Wizard - Select VHD/VHDX image format, VHD growable

    StarWind V2V Conversion Wizard - Select destination image file name

    StarWind V2V Conversion Wizard - Conversion progress 100% complete

    Now we can create a temporary virtual machine. Note that we stick with a Generation 1 VM (I tried Generation 2 and it didn’t work). Also, to keep file sizes down, I stuck with a .vhd file (not a .vhdx). A .vhdx file will work but they

    In an elevated prompt, run the following:

    New-VM -name "test-environment2019" -VHDPath C:\tmp\chocolatey-test-environment-disk001.vhd -Generation 1

    and you should see this output:

    Name                 State CPUUsage(%) MemoryAssigned(M) Uptime   Status             Version
    ----                 ----- ----------- ----------------- ------   ------             -------
    test-environment2019 Off   0           0                 00:00:00 Operating normally 11.0
    Set-VMProcessor -VMName test-environment2019 -Count 4
    Set-VM -VMName test-environment2019 -AutomaticCheckpointsEnabled $false -CheckpointType Disabled -AutomaticStopAction ShutDown

    Start the VM and wait for it to boot. Then sign in (the password is ‘vagrant’)

    Go to Settings, Apps and click on Oracle VM VirtualBox Guest Additions. Click Uninstall. Then click Yes to confirm. The VM will reboot.

    Once it has rebooted, you can shut down the VM.

    Run compress just for good measure

    Optimize-VHD -Path C:\tmp\chocolatey-test-environment-disk001.vhd -Mode Full

    We’re now following the steps outlined in the Vagrant documentation for creating a Hyper-V base box.

    Export the VM

    Export-VM -VMName test-environment2019 -path c:\tmp\v3

    Go to c:\tmp\v3 and delete the Snapshots folder (it’s probably empty anyway)

    Create a metadata.json file

    I took a look at the same file in the 2.0.0 box, and it turns out this is all it contains:

      "provider": "hyperv"

    Add that to the metadata.json file.

    Now we need to create a .tar file (this may take a few minutes). Tar has been included with Windows since late 2017, but you could also use 7-Zip or similar.

    cd C:\tmp\v3\test-environment2019\
    tar cvzf c:\tmp\test-environment2019.tar ./*

    Now we can add this to Vagrant using

    vagrant box add C:\tmp\test-environment2019.tar --provider hyperv --name chocolatey/test-environment

    You’ll see output similar to the following:

    ==> box: Box file was not detected as metadata. Adding it directly...
    ==> box: Adding box 'chocolatey/test-environment' (v0) for provider: hyperv
        box: Unpacking necessary files from: file:///C:/tmp/test-environment2019.tar
    ==> box: Successfully added box 'chocolatey/test-environment' (v0) for 'hyperv'!

    The one issue with this is that you can see the version number of this box is v0. I’d much prefer to set the version 3.0.0. It turns out you can’t set that directly via the command line, but there is a workaround.

    Create another metadata.json file (in c:\tmp) and add the following content:

      "name": "chocolatey/test-environment",
      "versions": [
          "version": "3.0.0",
          "status": "active",
          "providers": [
              "name": "hyperv",
              "url": "file:///C:/tmp/test-environment2019.tar"

    and add the new box to Vagrant using this file instead:

    vagrant box add .\metadata.json

    And now we see this output

    ==> box: Loading metadata for box '.\metadata.json'
        box: URL: file://C:/tmp/metadata.json
    ==> box: Adding box 'chocolatey/test-environment' (v3.0.0) for provider: hyperv
        box: Unpacking necessary files from: file:///C:/tmp/test-environment2019.tar
    ==> box: Successfully added box 'chocolatey/test-environment' (v3.0.0) for 'hyperv'!

    We can now list all the boxes Vagrant knows about:

    vagrant box list
    chocolatey/test-environment (hyperv, 0)
    chocolatey/test-environment (hyperv, 2.0.0)
    chocolatey/test-environment (hyperv, 3.0.0)
    chocolatey/test-environment (VirtualBox, 3.0.0)

    I just want the ‘hyperv 3.0.0’ box, so I’ll remove the others

    vagrant box remove chocolatey/test-environment --box-version 0 --provider hyperv
    vagrant box remove chocolatey/test-environment --box-version 2.0.0 --provider hyperv
    vagrant box remove chocolatey/test-environment --box-version 3.0.0 --provider VirtualBox

    And now you should be fine to run vagrant up to provision a new VM using the Hyper-V provider, and it will use Windows Server 2019!

    Here’s an example of doing this with the chocolatey-test-environment (run from an elevated prompt):

    vagrant up

    Which gives the following output (including signing in with your local username and password):

    Bringing machine 'default' up with 'hyperv' provider...
    ==> default: Verifying Hyper-V is enabled...
    ==> default: Verifying Hyper-V is accessible...
        default: Configuring the VM...
        default: Setting VM Integration Services
    ==> default: guest_service_interface is enabled
    ==> default: heartbeat is enabled
    ==> default: key_value_pair_exchange is enabled
    ==> default: shutdown is enabled
    ==> default: time_synchronization is enabled
    ==> default: vss is enabled
        default: Setting VM Enhanced session transport type to disabled/default (VMBus)
    Vagrant requires administrator access for pruning SMB shares and
    may request access to complete removal of stale shares.
    ==> default: Starting the machine...
    ==> default: Waiting for the machine to report its IP address...
        default: Timeout: 130 seconds
        default: IP:
    ==> default: Waiting for machine to boot. This may take a few minutes...
        default: WinRM address:
        default: WinRM username: vagrant
        default: WinRM execution_time_limit: PT2H
        default: WinRM transport: negotiate
    ==> default: Machine booted and ready!
    ==> default: Preparing SMB shared folders...
        default: You will be asked for the username and password to use for the SMB
        default: folders shortly. Please use the proper username/password of your
        default: account.
        default: Username (user[@domain]): david
        default: Password (will be hidden):
    Vagrant requires administrator access to create SMB shares and
    may request access to complete setup of configured shares.
    ==> default: Mounting SMB shared folders...
        default: C:/dev/git/chocolatey-test-environment/packages => /packages
        default: C:/dev/git/chocolatey-test-environment => /vagrant
    ==> default: Machine already provisioned. Run `vagrant provision` or use the `--provision`
    ==> default: flag to force provisioning. Provisioners marked to run always will still run.

    Windows Hyper-V Manager will show the new VM running:

    Windows Hyper-V Manager showing chocolatey-test-environment VM running

    You can also connect to the VM and sign in to confirm it is running Windows Server 2019 and working as expected:

    Screenshot of connection to virtual machine, showing 'About Windows' dialog with Windows Server 2019

    Vagrant error

    When you run vagrant up, it fails with the following error (observed with Vagrant 2.3.7):

    An error occurred executing a remote WinRM command.
    Shell: Cmd
    Command: hostname
    Message: Digest initialization failed: initialization error

    Apparently this problem is solved with Vagrant version 2.3.8. Ensure you’re you’re using Vagrant 2.3.8 or newer.

  • DDD Adelaide is back for 2023

    Back in 2019, Andrew and I ran the first ‘rebooted’ DDD Adelaide conference. The response from the Adelaide developer community was amazing, and we were all set to run again in 2020. For some reason, we had to put plans on hold for a few years, but I’m excited to announce that we are back for 2023!

    DDD Adelaide 2023 logo

    It’s awesome to have Claire Webber, Harnoor Bandesh, Isaac Mann and Will Turner join the organising team. Check out Isaac’s post about why he got involved.

    Tickets are on sale now, but numbers are limited, so get in quick!

    If you are interested in speaking, we are now accepting talk proposals. We are looking for a diverse range of speakers and topics. You don’t need to be an expert speaker, we are happy to help you prepare your talk.

    Finally, an event like this doesn’t happen without sponsors. We strive to keep the ticket price low so that it won’t be a barrier for anyone to attend. But there are a surprising number of expenses involved in running the event, and income from tickets doesn’t come close to covering the costs. That’s why we need sponsors, so if you work for a company that would like to support the Adelaide developer community, please get in touch.

    Call to action

    David and Andrew standing in front of a seated crowd at DDD 2019

    Hope to see you there! I’ll be the tall guy wearing the special edition ‘DDD’ Akubra 😊

  • HashiCorp Certified: Terraform Associate (003)

    I’ve been using Terraform quite a bit recently and noticed that HashiCorp have a Terraform Associate certification. Reviewing the exam objectives it sounded like it seemed to cover most of the things I’ve already been doing, so I decided to give it a go.

    Terraform certified associate badge

    The exam is run by PSI, so was a slightly different experience to those I’ve taken for Microsoft certifications. The sign-in process was a bit simpler (eg. scanning your ID with your webcam rather than having to upload them from your phone). The exam software required that I turn off a few background processes (OneDrive, a Zoom background process and the Virtual Machine Management Service). Once I’d done that the software was happy to proceed and when the proctor was satisfied with my room and desk setup I was able to start the exam.

    I finished the exam in good time and I was pleased to learn that I passed!

    The email summary of my results included a breakdown of how I went in each of the areas covered.

    Overall Score: 78%

    Breakdown by content area:

    1. Understand infrastructure as code (IaC) concepts: 100%
    2. Understand the purpose of Terraform (vs other IaC): 100%
    3. Understand Terraform basics: 87%
    4. Use Terraform outside the core workflow: 100%
    5. Interact with Terraform modules: 40%
    6. Use the core Terraform workflow: 88%
    7. Implement and maintain state: 72%
    8. Read, generate, and modify configuration: 63%
    9. Understand Terraform Cloud capabilities: 100%

    So looks like modules are an area I’m not as strong on! That’s fair as I haven’t made a lot of use of them so far.

    If you’re using Terraform, then I’d encourage you to go ahead and take the exam. Have a look at the study guide, sample questions and exam review to ensure you’re comfortable with all the topics being covered and how questions will be asked. Then register for the exam and give it a go!