Packaging COTS Applications for Windows

Habitat application packaging typically falls into one of two main categories:

  1. Packaging applications built from source code developed in-house or available via open source.
  2. Packaging commercial off the shelf (COTS) applications usually purchased from a third party vendor.

Habitat plan development patterns and issues to be considered at build and run time vary greatly between these two types of packaging. When it comes to the second class of packages – COTS – the techniques used in Linux are very different from Windows. Linux COTS packaging requires some understanding of ELF headers and patching them to point to Habitat dependencies. Windows binaries do not have ELF headers and use a different means of dynamic linking but there are many subtle and not so subtle nuances involved in packaging COTS applications very specific to Windows.

This post will discuss different high level approaches to take with Windows COTS applications and dive into some details on how to create a Habitat package that is isolatable, portable, and results in the fewest amount of system wide side effects as possible when running in a Habitat Supervisor.

Application Compatibility

There are two prerequisites that must be met to ensure that a COTS application can run in a Habitat Supervisor.

The Application Must Have a Silent Installer

This is almost never a problem. The vast majority of applications are capable of being silently installed. If it does not have a silent installer, you may be able to get by if you choose an approach of packaging without the installer. Read on for more about that.

If you must install via the application installer program and it has no silent install option, there is no automation tool, Habitat included, that can help.

The Application Must be Capable of Running on the Target OS

Again, this is usually not a problem. Windows does a great job when it comes to backwards compatibility and many Windows Server 2003 applications will run on Windows Server 2016. However there are absolutely legacy applications that cannot run on modern versions of Windows. Habitat does not employ any extra virtualization/emulation layer to make an application think it is running on an older operating system. For instance, 16 bit applications cannot run on a modern Windows version. There are other applications that may have hard coded checks to ensure they are running on a specific version or within a specific range of versions of Windows. SQL Server 2000 is an example of such an application. While it does not happen often, some Windows kernel APIs can change or be removed over time. If an application calls a Win32 API function with an outdated signature, that application may crash on a modern operating system.

Purity vs. Pragmatism

When developing a Windows Habitat package for a COTS application, there are typically one of two ways to approach the plan.ps1 and hooks:

  1. A Purist approach: Package run time artifacts remain in the Habitat file tree and do not affect external Habitat system state. Developing these can be challenging but have lots of benefits.

  2. A Pragmatic approach: The purist path is too hard, time consuming or down right impossible. Besides, one may not need strict isolation if the Habitat based services are the only applications running on the machine. In such a case, a more pragmatic approach is to just run the application installer binary in the init hook.

There is a bit of a sliding scale between these approaches but the above extremes reflect the spirit of these two packaging methodologies.

Now it may seem like if one can get by on simply packaging the installer and invoking its setup binary at run time (most likely in an init hook), why go to the trouble to develop a package that pulls out the installer’s binaries at build time and reverse engineer any logic the installer might have done at run time? Especially when this logic may be hidden away and almost impossible to reconstruct plainly in Windows COTS installers.

Let’s look at why it sometimes makes sense to do the hard thing and why it may make better sense to take the pragmatic route on other occasions.

The Virtues of Purity

Briefly, here are the benefits of the purist approach:

  • Faster service startup. The binaries are already extracted and there is no need to run a possibly lengthy installer process.
  • Fewer or no side effects. Loading such a package in the Supervisor will not contaminate disk space outside of /hab and will possibly not muddy up the registry or the persistable system environment variables.
  • Dependencies remain explicit and non magical. It’s entirely possible that an installer will install system wide dependencies such as:

    • C runtimes into System32
    • COM component registrations
    • Register .Net assemlies with the Global Assembly Cache (GAC)

Non-Habitat services outside of this package may be impacted by these dependencies.

It’s especially nice when developing packages in a local Windows Studio, to know that installing the package I am developing will not have any stateful impact on my machine. I can blow away the Studio and my machine remains unscathed. Of course a containerized Studio will avoid this contamination. However, especially when developing COTS packages, troubleshooting in a GUI based environment can be helpful.

Also, updates can be simplified by the purist approach. I don’t have to take pains to run an uninstaller or upgrade binary to clean the state of a previous version. My service simply points to the updated /hab/pkgs/ folder.

Now in the Linux world, achieving this kind of purity is much more straightforward. Process state in Linux is very much governed by what is on disk and in environment variables. Windows, on the other hand, has several global system wide APIs that are not easily sandboxed.

Giving Up

There are indeed times when it just is not worth it to take the above purist approach. This is especially true when it could take days to reverse engineer exactly what the installer is doing and you are willing to live with the consequences. The SQL Server (core/sqlserver) plan is a good example here. The SQL Server installer pumps volumes into the Windows registry and generates several files including its system database files at install time. Fortunately SQL Server has some isolation capabilities like “named instances” that our plan takes advantage of to limit (but not eliminate) system wide impact.

It’s also possible that your COTS application may be the only thing ever to run on its node in which case isolation is just a luxury and one you can afford to do without. If you plan to run the COTS application in a containerized Supervisor environment, you automatically get an isolation partition between your application and the host system.

Developing a Hook Installed Service Plan

If you have decided that the best option in your case is to simply install the COTS application using its own installer, here are some guidelines to follow:

  • Remember to invoke the installer in the init or run hook and not in the plan.ps1 build callback functions. What happens in the build callbacks happens on the build server and not at run time on the Supervisor node. If you are testing in a Studio, these two environments are essentially the same and it can be easy to get fooled into thinking that the application install is working and then wonder why the application is not installed when deploying your package to a Supervisor.

  • Be aware of the command line arguments that your application installer accepts. These may give you the option to minimize the impact to the system outside of the Habitat environment. For example, the SQL Server installer has many installation options that control where files are installed. It even allows you to use “Named Instances” that isolate one sql engine from another. This means I can have a named Habitat instance that will leave any existing database on the server alone.

Developing a Portable and Isolatable Plan

Now lets assume you have decided to take the “purist” route described above. The rest of this post will look at the nuts and bolts mechanics of how to actually do that.

Before you Start Coding

Before we start breaking the binaries out of the COTS installer, we need to understand what it does. It is easiest to do this on as clean of a system as possible – just a basic OS installation with no other applications. I also suggest doing this on a local hypervisor and snapshot the clean state so that you can easily and quickly restore to a clean state.

Install the application using its own installer. You can do this with its standard GUI wizard or if the application is normally installed from the command line with specific parameters, then install it using that approach. Install it in such a way that best emulates your normal deployment methodology. After the installation look to see how the state of the system has changed. Things to look for include:

  • Files in c:\Program Files, c:\Program Files (x86)
  • Windows services in the Services Management Console
  • New Environment Variables
  • Paths added to the PATH variable
  • Web app? – Added sites and pools in IIS
  • Added registry keys in HKLM:\SOFTWARE or HKLM:\SOFTWARE\WOW6432Node looking specifically for a subkey named after the vendor

While the above are the most likely system changes you will find, it’s also possible you could find these less common changes:

  • New tasks in the Windows Task Scheduler
  • New COM+ applications
  • Newly registered COM components

If you are familiar with the general nature of the application, that will help you to zero in on what to look for. The more you know about the app, the better and more clear the path forward will be. Is this a:

  • *.exe based tool or service one invokes directly?
  • Web Site running on IIS?
  • A background Windows Service?
  • A *.dll library or COM component (or several) to be used by a top level application?

You will want to make note of any changes you detect after install because your hooks will need to replicate them via Powershell. Also make sure the application actually works. You want to be confident that you are in the desired state that you hope your Habitat plan will reproduce.

Lastly, snapshot or checkpoint your VM here so you can easily and quickly return to a state where the application worked when things go poorly in your Habitat packaging.

Breaking Open the Installer

Regardless of the type of application being installed, extracting the relevant binaries from the installer file(s) is always going to be the first gating challenge. The method you use to do this can have several permutations depending on the type of installer you have. Unless it is an *.msi based installer, it will not be obvious what type of installer it is.

MSI Installers

Use core/lessmsi to extract the files inside of an .msi file.


function Invoke-Unpack {
  lessmsi x (Resolve-Path "$HAB_CACHE_SRC_PATH/$pkg_filename").Path
  mkdir "$HAB_CACHE_SRC_PATH/$pkg_dirname"
  Move-Item "cmake-$pkg_version-win64-x64/SourceDir/cmake" "$HAB_CACHE_SRC_PATH/$pkg_dirname"

lessmsi will extract the files into a directory named SourceDir. Make sure to use Resolve-Path on the msi file in order to send lessmsi the absolute and properly Windows formatted path. lessmsi does not like forward slashes.

Wix .exe Installers

Most .exe based installers (but not all) that come from the Microsoft downloads site seem to be WIX based installers. You can use the dark.exe binary in core/wix to extract its contents. Often these installers simply contain msi files; so you will then need to use lessmsi to extract the contents of those.


$pkg_build_deps=@("core/lessmsi", "core/wix")
$pkg_bin_dirs=@("Program Files\Microsoft SDKs\Windows\v10.0A\bin\NETFX 4.6.2 Tools\x64")
$pkg_lib_dirs=@("Program Files\Windows Kits\NETFXSDK\4.6.2\Lib\um\x64")
$pkg_include_dirs=@("Program Files\Windows Kits\NETFXSDK\4.6.2\Include\um")
function Invoke-Unpack {
  dark -x "$HAB_CACHE_SRC_PATH/$pkg_dirname" "$HAB_CACHE_SRC_PATH/$pkg_filename"
  Push-Location "$HAB_CACHE_SRC_PATH/$pkg_dirname"
  try {
    Get-ChildItem "AttachedContainer/packages" -Include *.msi -Recurse | % {
        lessmsi x $_
  finally { Pop-Location }
function Invoke-Install {
  Get-ChildItem "$HAB_CACHE_SRC_PATH/$pkg_dirname" -Include "Program Files" -Recurse | % {
    Copy-Item $_ "$pkg_prefix" -Recurse -Force

The only sure way to know if an exe is wix based is to use dark to extract its contents. If you get an error, it is not a wix installer.

Using 7zip to Extract an .exe Installer

Some *.exe installers can be expanded with core/7zip. Again, it’s hard to know if this will work without actually trying it.


function Invoke-Unpack() {
    New-Item "$HAB_CACHE_SRC_PATH/$pkg_dirname" -ItemType Directory | Out-Null
    Push-Location "$HAB_CACHE_SRC_PATH/$pkg_dirname"
    try {
        7z x "$HAB_CACHE_SRC_PATH/$pkg_filename"
        7z x
        7z x installerexe -ojava
    finally { Pop-Location }

This core/jre exe installer has an embedded file that contains a installerexe file which is what has the actual installer payload.

Unpacking an inno Installer

Inno is an application setup tool sometimes seen in the COTS world to create exe installers. If you open the .exe file in a text editor and search the junk text for “inno,” chances are this is an inno based installer. You can use core/innounp to extract an inno installer.

$pkg_build_deps = @("core/innounp")
function Invoke-Unpack {
    mkdir "$HAB_CACHE_SRC_PATH/$pkg_dirname"
    Push-Location "$HAB_CACHE_SRC_PATH/$pkg_dirname"
    try {
        innounp -x (Resolve-Path "$PLAN_CONTEXT/install.exe").Path
  Finally { Pop-Location }

When All Options Fail

If none of the above options manage to extract your .exe installer, its possible that the .exe file can be invoked with the right arguments that will extract its contents without actually performing an application install. The trick is finding out what those args are. I usually try to find any cli help for the exe by passing --help, -h, /help, /h, /?, -? to the installer until I get some help. Here is an example of a exe that provides an argument to simply extract the contents.

Start-Process "$HAB_CACHE_SRC_PATH/$pkg_filename" -Wait -ArgumentList "--passive --layout $HAB_CACHE_SRC_PATH/$pkg_dirname --lang en-US"

This exe exposes a --passive argument to suppress user interaction and a --layout argument to specify a location where the contents should be extracted to (“layed out”).

Common Application Install and Configuration Scenarios

Now that you have managed to pull the raw binaries and other support files out of the installer, what steps do we take to order and further manipulate them so that we have a functioning application managed in Habitat? That is largely going to depend on the type of application you are packaging. In some cases, like with many command line tools and services, this could be super simple – just copy the binaries into the package and add them to pkg_bin_dirs. In other cases you may need to add code to your init or run hooks to install a Windows Service, set registry keys, and maybe apply some DSC configuration resources. Let’s walk through some of the more common scenarios.

Command Line Executables

These are often the simplest applications to package. They typically just need a run hook to invoke the exe and possibly pass in some config data or a configuration file. This scenario reflects what we are used to in most Linux based applications and allows us to maintain a purely side-effect free habitat package. See this Windows based MySQL plan as an example.

If the executable is not a “top level” application but a tool used as a runtime or build dependency, you do not even need hooks. Just make sure the executables are on the path:


$pkg_description="Node.js® is a JavaScript runtime built on Chrome's V8 JavaScript engine."
$pkg_maintainer="The Habitat Maintainers 

Here by simply ensuring that node.exe is in pkg_bin_dirs, other node applications can depend on this and expect invoking node to invoke the executable in this package.

Windows Service Applications

If the application runs as a Windows Service, you are going to want to install the service in your init hook. However the first question to ask is: does this service REALLY need to run as a service? The answer to this question may very well be “no.” If it is indeed “no” then the best option is to just run it as a normal executable, which puts us back into the scenario above.

Many Windows service based binaries are capable of running in console mode. That is normally not ideal for a service that you want to run unattended in the background, but that is what the Habitat Supervisor is for. Since the Supervisor can run as a Windows service, you can have it run the executable in console mode but get service-like behavior without creating a system-wide Windows service. This just requires that the service executable can indeed be run directly and that it responds to ctrl+c events for stopping the service.

For services that do not meet the above criteria and must be run as a true Windows service, you can add the service in the init hook:


Set-Location {{pkg.svc_path}}
if(Test-Path bin) { Remove-Item bin -Recurse -Force }
New-Item -Name bin -ItemType Junction -target "{{pkg.path}}/bin" | Out-Null
if((Get-Service my_service -ErrorAction SilentlyContinue) -eq $null) {
    &$env:systemroot\system32\sc.exe create my_service binpath= (Resolve-Path "{{pkg.svc_path}}\bin\MyService.exe").Path

It is important that you do not configure the service start mode to automatic and keep it at the default manual setting because we want the Supervisor to manage its lifecycle.

Rather than directly invoking the executable, your run hook will manage the service start and stop commands.


try {
    Start-Service my_service
    Write-Host "{{}} is running"
    while($(Get-Service my_service).Status -eq "Running") {
        Start-Sleep -Seconds 1
finally {
    # The service will still be running if the supervisor is stopping the service
    Write-Host "{{}} is stopping..."
    if($(Get-Service my_service).Status -ne "Stopped") {
        Stop-Service my_service
    Write-Host "{{}} has stopped"

If your service requires environmental variables to be set, you cannot simply set them in the run hook like you could if you were calling the executable directly. Because the Windows service process is not a child process of the hook, you must unfortunately set these environment variables persistently.


Write-Host "Setting up environment variables!"
{{#each cfg.env_variables}}
    [Environment]::SetEnvironmentVariable("{{@key}}", "{{this}}", [System.EnvironmentVariableTarget]::Machine)

Setting Registry Values

Some COTS applications require Windows Registry keys to be created which are later referenced by the application. These are usually located somewhere under HKLM:\SOFTWARE under a key named after the software vendor.

If the application just requires a couple keys, it’s probably easiest to add them individually in an init or run hook.


Set-ItemProperty -Path  "HKLM:\SOFTWARE\Acme\SuperService" -Name DataPath -Value (Resolve-Path "{{pkg.svc_data_path}}").Path

If the values could possibly change upon a reconfigure, set them in the run hook so that the reconfigured values will update the registry.

If there is a substantial tree of keys and subkeys that the application requires, it’s easiest to export the entire tree to a .reg file. The file can then be templatized in the config directory.


Windows Registry Editor Version 5.00
"ProdDesc"="IBM Tivoli Monitoring: Windows OS Agent"

The init or run hook would then import this template.


reg.exe import "{{pkg.svc_config_path}}\tivoli.reg"

Website Configuration

If your application runs as a web application, unless it is running an embedded web server, it is likely you will need to configure an IIS Application Pool and Website.

Take a good look at the IIS Management Console where the app is successfully running and observe what pools and sites are dedicated to these apps. For a comprehensive view at these individual entities, look at C:\Windows\System32\inetsrv\Config\applicationHost.config. This configuration file will include all of the configuration details without the need for alot of pointing and clicking.

You can express these IIS entities in your plan using Powershell DSC. See this Legacy ASP.NET plan as an example DSC configuration for configuring IIS. To wire up the configuration, make sure to declare a run time dependency on core/dsc-core and invoke its Start-DscCore function in the run hook to actually apply the configuration on the node.


Import-Module "{{pkgPathFor "core/dsc-core"}}/Modules/DscCore"
Start-DscCore (Join-Path {{pkg.svc_config_path}} website.ps1) NewWebsite

COM Registration

COM registration is becoming less and less frequent but many Legacy Windows applications have COM based dependencies. Especially if multiple applications depend on a COM component, it’s best to package that component separately. An example COM based binary in our core-plans repository is the sql-dmo package.

Consuming application service packages would declare a run time dependency on such a package and register it in their init hook.


."$env:SystemRoot\SysWow64\regsvr32.exe" /s "{{pkgPathFor "core/sql-dmo"}}\Program Files (x86)\Microsoft SQL Server\80\Tools\Binn\sqldmo.dll"

Note that the above uses the SysWow64 version (32-bit) of the regsvr32 tool which again is common in legacy 32 bit application scenarios. If you were registering the component for a 64-bit application, you would simply call the regsvr32.exe directly on the path.

The Build…Fix…Build…Fix…Build…Run Pattern

Especially when you are packaging an application about which you have little knowledge, your initial builds may fail inside of a Supervisor. Sometimes the Supervisor output makes it clear that the service is failing and at other times it may appear as though the hooks executed without error, but the application is not behaving as expected or just isn’t running at all.

The path forward in these cases is not always straight forward and we cannot document every edge case here. You will often need to use some creativity and put on your detective hat. Google and StackOverflow may be your best resources, but here are some tips to guide you as you attempt to solve your application packaging dilemmas.

Read the Logs

Which logs? Any logs and all the logs. Look for directories called log or logs. Check the system and application Windows Event Logs. These will often have the best clues to help you get to the root of the problem. Sometimes it helps to compare these logs to the logs on a system with a succesfully installed application.

Look for Missing or Misconfigured Configuration Files

Some installers may create or write to text files and inject configuration settings like listening port or the location of the installation directory. So look for text files that look like they store key/value pairs. They could be json, xml, toml, yaml, or a proprietary format. If you find these and it looks as though their data is incorrect or missing, you may need to add these files to your plan’s config directory and have the Supervisor inject the correct data at run time and then have your hooks copy or link them to the location where the application expects them to be.

Use Process Monitor to Discover Missing Files or the Paths where your Application is Searching for Files

The application logs may possibly include errors indicating that a file cannot be found, or simply stating that “a file” cannot be found without the courtesy of including the name of the file. You may be missing a dependency or your application is searching the wrong directories for certain files.

Process Monitor (or procmon) can be very helpful in solving this problem. It will watch all file activity under a specific process. Just before loading your service in the Supervisor, have procmon watch your service process. Stop it right after things fail. Now look for files that it was not able to open. Often you will see it looking in several directories for the same file before it gives up. If you know the file name ahead of time, you can add a procmon filter to only include paths that contain the file name.

Maybe you discover that the file it is looking for actually exists in the Habitat package’s svc_path but the application is looking somewhere else – like c:\Program Files. This often indicates an incorrect or missing configuration somewhere. It can be helpful to load the entire application directory into an editor like vscode and do a global search for the filename or perhaps c:\Program Files. This might surface potential configuration files that you need to templatize in your Habitat plan.

Use Process Explorer to Discover the Environment Variables Loaded in a Process

Process Explorer (procexp) is another tool that can provide some visibility into a process environment. When an application is failing, it may have missing or misconfigured environment variables. Process explorer displays all running processes on a system and allows you to drill into each and observe some basic information about the process. Look at the directory where the process is running from and look at its environment variables. Do you see anything obviously wrong? Do they vary in a meaningful way from the environment variables inside an application that is running correctly?

Know When to Stop

Purity is great but obsession often ends poorly. If you find that deconstructing an installer is sucking up too much time or crushing your soul, strongly consider the “installer in the hook” approach. Remember that in the end, Habitat should be saving you time and trouble and not adding extra burden to your deployments!

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Matt Wrock

I am a software developer for Chef and much of my focus has been making Chef better on Windows. When not developing Chef code, I'm usually contributing to other projects in the Chef ecosystem. I regularly contribute to the WinRM gem and Vagrant, I am a member of the core Chocolatey team, author of Boxstarter and was an early contributor to Pester creating its Powershell Mocking functionality. I am a former Microsoft engineer and write regularly on Windows automation topics at