It might not be found on a curated list of urban legends, but trust me, IT IS possible (!!!) to fully automate the building and configuration of Windows virtual machines for AWS.  While Windows Server may not be your first choice of operating systems for immutable infrastructure, sometimes you as the IT professional are not given the choice due to legacy environments, limited resources for re-platforming, corporate edicts, or lack of internal *nix knowledge.

Complain all you like, but after the arguing, fretting, crying, and gnashing of teeth is done, at some point you will still need to build an automated deployment pipeline that requires Windows Server 2016.  With some PowerShell scripting and HashiCorp Packer, it is relatively easy and painless to securely build and configure Windows AMIs for your particular environment regardless of environment variables.

Configuration Options

Let’s dig into an example of how to build a custom configured Windows Server 2016 AMI.  You will need access to an AWS account and have sufficient permissions to create and manage EC2 instances.  If you need an AWS account, you can create one for free.

I am using VS Code and built-in terminal with Windows Subsystem for Linux to create the Packer template and run Packer, however Packer is available for several many Linux distros, Mac OS, and Windows.

First, download and unzip Packer:

~/packer-demo:\> wget 
Resolving (,,, ... 
Connecting to (||:443... connected. 
HTTP request sent, awaiting response... 200 OK 
Length: 28851840 (28M) [application/zip] 
Saving to: ‘’ 
‘’ saved [28851840/28851840] 
~/packer-demo:\> unzip 
 inflating: packer

Now that we have Packer unzipped, verify that it is executable by checking the version:

~/packer-demo:\> packer --version

Packer can build machine images for a number of different platforms.  We will focus on the amazon-ebs builder, which will create an EBS-backed AMI.  At a high level, Packer performs these steps:

  1. Read configuration settings from a json file
  2. Uses the AWS API to stand up an EC2 instance
  3. Connect to the instance and provision it
  4. Shut down and snapshot the instance
  5. Create an Amazon Machine Image (AMI) from the snapshot
  6. Clean up the mess

The amazon-ebs builder can create temporary keypairs, security group rules, and establish a basic communicator for provisioning.  However, in the interest of tighter security and control, we will want to be prescriptive for some of these settings and use a secure communicator to reduce the risk of eavesdropping while we provision the machine.

There are two communicators Packer uses to upload scripts and files to a virtual machine: SSH (the default) and WinRM.  While there is a nice Win32 port of OpenSSH for Windows, it is not currently installed by default on Windows machines, but WinRM is available natively in all current versions of Windows, so we will use that to provision our Windows Server 2016 machine.

Let’s create and edit the userdata file that Packer will use to bootstrap the EC2 instance:

Set-ExecutionPolicy -ExecutionPolicy Unrestricted -Scope LocalMachine -Force -ErrorAction Ignore
$ErrorActionPreference = "stop"
# Remove any existing Windows Management listeners
Remove-Item -Path WSMan:\Localhost\listener\listener* -Recurse
# Create self-signed cert for encrypted WinRM on port 5986
$Cert = New-SelfSignedCertificate -CertstoreLocation Cert:\LocalMachine\My -DnsName "packer-ami-builder"
New-Item -Path WSMan:\LocalHost\Listener -Transport HTTPS -Address * -CertificateThumbPrint $Cert.Thumbprint -Force
# Configure WinRM
cmd.exe /c winrm quickconfig -q
cmd.exe /c winrm set "winrm/config" '@{MaxTimeoutms="1800000"}'
cmd.exe /c winrm set "winrm/config/winrs" '@{MaxMemoryPerShellMB="1024"}'
cmd.exe /c winrm set "winrm/config/service" '@{AllowUnencrypted="false"}'
cmd.exe /c winrm set "winrm/config/client" '@{AllowUnencrypted="false"}'
cmd.exe /c winrm set "winrm/config/service/auth" '@{Basic="true"}'
cmd.exe /c winrm set "winrm/config/client/auth" '@{Basic="true"}'
cmd.exe /c winrm set "winrm/config/service/auth" '@{CredSSP="true"}'
cmd.exe /c winrm set "winrm/config/listener?Address=*+Transport=HTTPS" "@{Port=`"5986`";Hostname=`"packer-ami-builder`";CertificateThumbprint=`"$($Cert.Thumbprint)`"}"
cmd.exe /c netsh advfirewall firewall add rule name="WinRM-SSL (5986)" dir=in action=allow protocol=TCP localport=5986
cmd.exe /c net stop winrm
cmd.exe /c sc config winrm start= auto
cmd.exe /c net start winrm

There are four main things going on here:

  1. Set the execution policy and error handling for the script (if an error is encountered, the script terminates immediately)
  2. Clear out any existing WS Management listeners, just in case there are any preconfigured insecure listeners
  3. Create a self-signed certificate for encrypting the WinRM communication channel, and then bind it to a WS Management listener
  4. Configure WinRM to:
    • Require an encrypted (SSL) channel
    • Enable basic authentication (usually this not secure as the password goes across in plain text, but we are forcing encryption)
    • Configure the listener to use port 5986 with the self-signed certificate we created earlier
    • Add a firewall rule to open port 5986

Now that we have userdata to bootstrap WinRM, let’s create a Packer template:

~/packer-demo:\> touch windows2016.json

Open this file with your favorite text editor and add this text:

    "variables": {
        "build_version": "{{isotime \"2006.01.02.150405\"}}",
        "aws_profile": null,
        "vpc_id": null,
        "subnet_id": null,
        "security_group_id": null
    "builders": [
            "type": "amazon-ebs",
            "region": "us-west-2",
            "profile": "{{user `aws_profile`}}",
            "vpc_id": "{{user `vpc_id`}}",
            "subnet_id": "{{user `subnet_id`}}",
            "security_group_id": "{{user `security_group_id`}}",
            "source_ami_filter": {
                "filters": {
                    "name": "Windows_Server-2016-English-Full-Base-*",
                    "root-device-type": "ebs",
                    "virtualization-type": "hvm"
                "most_recent": true,
                "owners": [
            "ami_name": "WIN2016-CUSTOM-{{user `build_version`}}",
            "instance_type": "t3.xlarge",
            "user_data_file": "userdata.ps1",
            "associate_public_ip_address": true,
            "communicator": "winrm",
            "winrm_username": "Administrator",
            "winrm_port": 5986,
            "winrm_timeout": "15m",
            "winrm_use_ssl": true,
            "winrm_insecure": true

Couple of things to call out here.  First, the variables block at the top references some values that are needed in the template.  Insert values here that are specific to your AWS account and VPC:

  • aws_profile: I use a local credentials file to store IAM user credentials (the file is shared between WSL and Windows). Specify the name of a credential block that Packer can use to connect to your account.  The IAM user will need permissions to create and modify EC2 instances, at a minimum
  • vpc_id: Packer will stand up the instance in this VPC
  • aws_region: Your VPC should be in this region. As an exercise, change this value to be set by a variable instead
  • user_data_file: We created this file earlier, remember? If you saved it in another location, make sure the path is correct
  • subnet_id: This should belong to the VPC specified above. Use a public subnet if needed if you do not have a Direct Connect
  • security_group_id: This security group should belong to the VPC specified above. This security group will be attached to the instance that Packer stands up.  It will need, at a minimum, inbound TCP 5986 from where Packer is running

Next, let’s validate the template to make sure the syntax is correct, and we have all required fields:

~/packer-demo:\> packer validate windows2016.json
Template validation failed. Errors are shown below.
Errors validating build 'amazon-ebs'. 1 error(s) occurred:
* An instance_type must be specified

Whoops, we missed instance_type.  Add that to the template and specify a valid EC2 instance type.  I like using beefier instance types so that the builds get done quicker, but that’s just me.

            "ami_name": "WIN2016-CUSTOM-{{user `build_version`}}",
            "instance_type": "t3.xlarge",
            "user_data_file": "userdata.ps1",

Now validate again:

~/packer-demo:\> packer validate windows2016.json
Template validated successfully.

Awesome.  Couple of things to call out in the template:

  • source_ami_filter: we are using a base Amazon AMI for Windows Server 2016 server. Note the wildcard in the AMI name (Windows_Server-2016-English-Full-Base-*) and the owner (801119661308).  This filter will always pull the most recent match for the AMI name.  Amazon updates its AMIs about once a month
  • associate_public_ip_address: I specify true because I don’t have Direct Connect or VPN from my workstation to my sandbox VPC. If you are building your AMI in a public subnet and want to connect to it over the internet, do the same
  • ami_name: this is a required property, and it must also be unique within your account. We use a special function here (isotime) to generate a timestamp, ensuring that the AMI name will always be unique (e.g. WIN2016-CUSTOM-2019.03.01.000042)
  • winrm_port: the default unencrypted port for WinRM is 5985. We disabled 5985 in userdata and enabled 5986, so be sure to call it out here
  • winrm_use_ssl: as noted above, we are encrypting communication, so set this to true
  • winrm_insecure: this is a rather misleading property name. It really means that Packer should not check if encryption certificate is trusted.  We are using a self-signed certificate in userdata, so set this to true to skip certificate validation

Now that we have our template, let’s inspect it to see what will happen:

~/packer-demo:\> packer inspect windows2016.json
Optional variables and their defaults:
  aws_profile       = default
  build_version     = {{isotime "2006.01.02.150405"}}
  security_group_id = sg-0e1ca9ba69b39926
  subnet_id         = subnet-00ef2a1df99f20c23
  vpc_id            = vpc-00ede10ag029c31e0
Note: If your build names contain user variables or template
functions such as 'timestamp', these are processed at build time,
and therefore only show in their raw form here.

Looks good, but we are missing a provisioner!  If we ran this template as is, all that would happen is Packer would make a copy of the base Windows Server 2016 AMI and make you the owner of the new private image.

There are several different Packer provisioners, ranging from very simple (the windows-restart provisioner just reboots the machine) to complex (the chef client provisioner installs chef client and does whatever Chef does from there).  We’ll run a basic powershell provisioner to install IIS on the instance, reboot the instance using windows-restart, and then we’ll finish up the provisioning by executing sysprep on the instance to generalize it for re-use.

We will use the PowerShell cmdlet Enable-WindowsOptionalFeature to install the web server role and IIS with defaults, add this text to your template below the builders [ ] section:

"provisioners": [
            "type": "powershell",
            "inline": [
                "Enable-WindowsOptionalFeature -Online -FeatureName IIS-WebServerRole",
                "Enable-WindowsOptionalFeature -Online -FeatureName IIS-WebServer"
            "type": "windows-restart",
            "restart_check_command": "powershell -command \"& {Write-Output 'Machine restarted.'}\""
            "type": "powershell",
            "inline": [
                "C:\\ProgramData\\Amazon\\EC2-Windows\\Launch\\Scripts\\InitializeInstance.ps1 -Schedule",
                "C:\\ProgramData\\Amazon\\EC2-Windows\\Launch\\Scripts\\SysprepInstance.ps1 -NoShutdown"

Couple things to call out about this section:

  • The first powershell provisioner uses the inline Packer simply appends these lines in order into a file, then transfers and executes the file on the instance using PowerShell
  • The second provisioner, windows-restart, simply reboots the machine while Packer waits. While this isn’t always necessary, it is helpful to catch instances where settings do not persist after a reboot, which was probably not your intention
  • The final powershell provisioner executes two PowerShell scripts that are present on Amazon Windows Server 2016 AMIs and part of the EC2Launch application (earlier versions of Windows use a different application called EC2Config). They are helper scripts that you can use to prepare the machine for generalization, and then execute sysprep

After validating your template again, let’s build the AMI!

~/packer-demo:\> packer validate windows2016.json
Template validated successfully.
~/packer-demo:\> packer build windows2016.json
amazon-ebs output will be in this color.
==> amazon-ebs: Prevalidating AMI Name: WIN2016-CUSTOM-2019.03.01.000042
    amazon-ebs: Found Image ID: ami-0af80d239cc063c12
==> amazon-ebs: Creating temporary keypair: packer_5c78762a-751e-2cd7-b5ce-9eabb577e4cc
==> amazon-ebs: Launching a source AWS instance...
==> amazon-ebs: Adding tags to source instance
    amazon-ebs: Adding tag: "Name": "Packer Builder"
    amazon-ebs: Instance ID: i-0384e1edca5dc90e5
==> amazon-ebs: Waiting for instance (i-0384e1edca5dc90e5) to become ready...
==> amazon-ebs: Waiting for auto-generated password for instance...
    amazon-ebs: It is normal for this process to take up to 15 minutes,
    amazon-ebs: but it usually takes around 5. Please wait.
    amazon-ebs: Password retrieved!
==> amazon-ebs: Using winrm communicator to connect:
==> amazon-ebs: Waiting for WinRM to become available...
    amazon-ebs: WinRM connected.
    amazon-ebs: #> CLIXML
    amazon-ebs: System.Management.Automation.PSCustomObjectSystem.Object1Preparing modules for first 
use.0-1-1Completed-1 1Preparing modules for first use.0-1-1Completed-1 
==> amazon-ebs: Connected to WinRM!
==> amazon-ebs: Provisioning with Powershell...
==> amazon-ebs: Provisioning with powershell script: /tmp/packer-powershell-provisioner561623209
    amazon-ebs: Path          :
    amazon-ebs: Online        : True
    amazon-ebs: RestartNeeded : False
    amazon-ebs: Path          :
    amazon-ebs: Online        : True
    amazon-ebs: RestartNeeded : False
==> amazon-ebs: Restarting Machine
==> amazon-ebs: Waiting for machine to restart...
    amazon-ebs: Machine restarted.
    amazon-ebs: EC2AMAZ-LJV703F restarted.
    amazon-ebs: #> CLIXML
    amazon-ebs: System.Management.Automation.PSCustomObjectSystem.Object1Preparing modules for first 
==> amazon-ebs: Machine successfully restarted, moving on
==> amazon-ebs: Provisioning with Powershell...
==> amazon-ebs: Provisioning with powershell script: /tmp/packer-powershell-provisioner928106343
    amazon-ebs: TaskPath                                       TaskName                          State
    amazon-ebs: --------                                       --------                          -----
    amazon-ebs: \                                              Amazon Ec2 Launch - Instance I... Ready
==> amazon-ebs: Stopping the source instance...
    amazon-ebs: Stopping instance, attempt 1
==> amazon-ebs: Waiting for the instance to stop...
==> amazon-ebs: Creating unencrypted AMI WIN2016-CUSTOM-2019.03.01.000042 from instance i-0384e1edca5dc90e5
    amazon-ebs: AMI: ami-0d6026ecb955cc1d6
==> amazon-ebs: Waiting for AMI to become ready...
==> amazon-ebs: Terminating the source AWS instance...
==> amazon-ebs: Cleaning up any extra volumes...
==> amazon-ebs: No volumes to clean up, skipping
==> amazon-ebs: Deleting temporary keypair...
Build 'amazon-ebs' finished.
==> Builds finished. The artifacts of successful builds are:
==> amazon-ebs: AMIs were created:
us-west-2: ami-0d6026ecb955cc1d6

The entire process took approximately 5 minutes from start to finish.  If you inspect the output, you can see where the first PowerShell provisioner installed IIS (Provisioning with powershell script: /tmp/packer-powershell-provisioner561623209), where sysprep was executed (Provisioning with powershell script: /tmp/packer-powershell-provisioner928106343) and where Packer yielded the AMI ID for the image (ami-0d6026ecb955cc1d6) and cleaned up any stray artifacts.

Note: most of the issues that occur during a Packer build are related to firewalls and security groups.  Verify that the machine that is running Packer can reach the VPC and EC2 instance using port 5986.  You can also use packer build -debug win2016.json to step through the build process manually, and you can even connect to the machine via RDP to troubleshoot a provisioner.

Now, if you launch a new EC2 instance using this AMI, it will already have IIS installed and configured with defaults.  Building and securely configuring Windows AMIs with Packer is easy!

For help getting started securely building and configuring Windows AMIs for your particular environment, contact us.

-Jonathan Eropkin, Cloud Consultant