Building Windows images with Packer

Hi, folks!

Sometimes you need to create a base or custom image to use one in any kind of automated deployments (CD pipelines, Dev, QA  and etc.) in cloud or on-premises environments. Then, you might start searching for a good solution to make your task easier. Built-in sysprep?  Well, it’s a classic way for Windows without any additional functionality that might be required especially for clouds. So, what can be used for such task?  Definitely, Packer from HashiCorp would be one of the best tool. It allows you to build your custom image from Marketplace image (as for example) and place that image to the Azure Images for further usage.

In the JSON-example below, Packer uses provided options for authentication (variable section) and passes them to the Azure Resource Manager builder section. Packer supports a bunch of builders such as Azure, Hyper-V, VMware or AWS . In my case, Packer uses Azure RM and it’s Windows Server 2019-Datacenter marketplace image, creates a VM, connects to the VM via communicator (see communicator subsection), and then prepares image by running scripts and actions defined in the provisioners section.  I’m using here two PowerShell scripts for installing IIS role and OS sysprepping at the end of customization. Also, packer automatically updates OS and restarts it if necessary (custom windows-update and built-in windows-restart provisioners)

    "variables": {
        "client_id": "service principal|id here",
        "client_secret": "service principal| secret here",
        "tenant_id": "AD tenant's id here",
        "subscription_id": "subscription's id here"
    "builders": [
            "type": "azure-arm",
            "client_id": "{{user `client_id`}}",
            "client_secret": "{{user `client_secret`}}",
            "tenant_id": "{{user `tenant_id`}}",
            "subscription_id": "{{user `subscription_id`}}",
            "os_type": "Windows",
            "image_publisher": "MicrosoftWindowsServer",
            "image_offer": "WindowsServer",
            "image_sku": "2019-Datacenter",
            "image_version": "latest",
            "managed_image_resource_group_name": "TestRG",
            "managed_image_name": "ws2019-iis",
            "disk_caching_type": "ReadWrite",
            "communicator": "winrm",
            "winrm_use_ssl": true,
            "winrm_insecure": true,
            "winrm_timeout": "20m",
            "winrm_username": "packer",
            "location": "West Europe",
            "vm_size": "Standard_A2_v2",
            "azure_tags": {
                "dept": "IT"
    "provisioners": [
            "type": "powershell",
            "inline": [
                "Write-Host 'Configuring IIS Role and sysprepping...'"
            "type": "powershell",
            "script": "./scripts/iis-install.ps1"
            "type": "windows-update"
            "type": "windows-restart"
            "type": "powershell",
            "script": "./scripts/iis-sysprep.ps1"

When you end up with the configuration file, run packer build and wait while customization steps finish. Packer’s basic steps for a build are:

  • Create a resource group.
  • Validate and deploy a VM template.
  • Execute provision – defined by the user; typically shell commands.
  • Power off and capture the VM.
  • Delete the resource group.
  • Delete the temporary VM’s OS disk.

As a result, image with the name defined in the managed_image_name option will be added to Azure Images service:

packer azure images

Scripts and other stuff will be available on my GitHub soon. Stay tuned.

Using IIS as a reverse proxy for Jenkins

Howdy, guys! Today, I’d like to show you how to configure IIS along with ARR to publish and secure your Jenkins portal with HTTPS and SSL. Going forward, make sure that your site name (, in my case) is publicly available (every external Certificate Authority requires domain validation before generating a SSL-certificate for your site. Otherwise, you can use a self-signed certificate for demo purposes (as it shown later in this post).

TIP: to get a SSL-certificate, you can use a completely free Let’s Encrypt CA (windows ACME tool located here , download it and extract the archive, and then run the wacs.exe application to create new certificate (see the screenshot below)) or comodo free SSL certificate for 90 days . Be careful! LetsEncrypt has some rate limits. For example, there is a Failed Validation limit of 5 failures per account, per hostname, per hour and if you’ve hit a rate limit, you don’t have a way to temporarily reset it. You’ll need to wait until the rate limit expires after a week

Prepare your environment

  • Install and configure Jenkins (it it’s not yet done)
  • Add Web Server (IIS) server role with the default settings + HTTP Redirection and WebSocket Protocol

Install-WindowsFeature Web-Server,Web-WebServer,Web-Common-Http,Web-Default-Doc,Web-Dir-Browsing,Web-Http-Errors,Web-Static-Content,Web-Http-Redirect,Web-Health,Web-Http-Logging,Web-Performance,Web-Stat-Compression,Web-Security,Web-Filtering,Web-App-Dev,Web-WebSockets,Web-Mgmt-Tools,Web-Mgmt-Console -IncludeManagementTools

  • Download and install URL Rewrite and IIS ARR
  • My machine is not in the domain, so I need to edit my hosts file (C:\Windows\System32\drivers\etc\hosts) and add a new line as follows:
  • Create a self-signed certificate or use the certificate provided by public CA (as we briefly discussed in the beginning). I also recommend to add created certificate to the Trusted Root Certification Authorities to avoid any warning messages in browsers.

New-SelfSignedCertificate -DnsName "" -CertStoreLocation "cert:\LocalMachine\My"

Configure IIS and ARR

Open IIS manager (InetMgr.exe), go to the Default Web Site – Actions – Bindings and add a new site binding for HTTPS type (use the certificate created earlier). Then, edit HTTP binding by typing a hostname (might be used by ACME tool while generating a certificate)

Click on the IIS server name, go to Application Request Routing Cache – Server Proxy Settings and Enable the Proxy, disable
Reverse rewrite host in response header , and then click Apply

Navigate to the Default Web Site – URL Rewrite -View Server Variables... and add the a new variable named as HTTP_FORWARDED.

Go back to rules, and add a new reverse proxy rule, type a site name (, in my case) and click OK. Doble-click on the created rule and define a condition input {CACHE_URL} with the following pattern ^(http|ws)s:// , and then add server variable HTTP_FORWARDED with the following value for={REMOTE_ADDR};by={LOCAL_ADDR};host=”{HTTP_HOST}”;proto=”https”

Then, we need to define how to rewrite URL under action:
and remove the Append query string check

Go to Application Pools and change .NET CLR Version to No Managed Code

Then go back to the Default Web Site and select Request Filtering – Edit Feature Settings and turn on Allow double escaping

In the Default Web Site → Configuration Editor change the Section to system.webServer/rewrite/rules , and change useOriginalURLEncoding to False

Configure Jenkins

Once you finished with IIS/ARR configuration, we need to set Jenkins to enable the proxy and work with a new URL (, in my case). Carry out the following steps:

  1. Open Jenkins portal, go to Manage Jenkins – Configure Global Security enable Prevent Cross Site Request Forgery exploits and proxy compatibility
  2. In the Configure System, define a new URL under Jenkins location that should be used by Jenkins (, in my case), and then apply the changes
  3. Open a new tab in the browser and verify that you can access the Jenkins by using the new URL and HTTPS


P.S. this post is based on the wiki article that contains a bit more details