Latest News

Essential Know-How from a Packaging Expert to Overcome Windows Application Deployment Challenges

The application packaging and deployment sector is experiencing a dynamic shift, driven by emerging technologies and evolving best practices.

Understanding the multifaceted trends reshaping this industry is essential. Key developments like the integration of cloud computing and containerization technologies, robust security measures, and the adoption of DevOps and Agile methodologies are shaping the future of application packaging and deployment.

In this dynamic environment, the role of application packaging experts is evolving, demanding a blend of technical prowess, strategic thinking, and adaptability. The future of the industry promises to be as challenging as it is exciting, with innovations and developments continually reshaping the landscape.

In this article, we address challenges like managing dependencies, ensuring secure deployments, and handling rapid version updates, shedding light on the key trends and factors shaping the future direction of application packaging and deployment. We will also provide expert insights to help professionals navigate these challenges effectively.

If you’re interested in learning more about application packaging, be sure to check out our Application Packaging Process – The End-to-End Guide article.

Now, let’s dive deeper into the specifics of application deployment to gain a better understanding of these processes.

Understanding Application Deployment

In an enterprise environment, application deployment refers to the process of distributing and installing software applications throughout the organization’s infrastructure, ensuring availability for end-users or other systems.

This multi-step process includes:

  • preparing the application for deployment,
  • configuring the deployment environment,
  • carrying out the deployment process,
  • and confirming the application functions effectively in the production environment.

Core Keys of Effective Application Deployment

Having established a foundation for what application deployment entails, let’s now explore the broad range of aspects involved in executing this process effectively.

Package Request

Commonly known as a change request, the initial step in application deployment involves identifying the need for deploying an application, whether it is a new version or an update.

Usually, it involves a package request form or order document that specifies the application to be deployed and outlines any customization settings that need to be applied alongside the application.

Preparation Phase

During this stage, the application undergoes preparation for deployment. This involves compiling the code, packaging it, resolving any dependencies, and creating deployment artifacts. Furthermore, configuration settings and environment-specific parameters are defined.

Deployment Planning

Enterprises typically adhere to established deployment processes and guidelines. This phase entails identifying target environments, selecting the appropriate deployment methods (such as manual or automated), and assessing potential risks or dependencies that could impact the deployment process.

Testing and Quality Assurance

Before deploying to the production environment, rigorous testing and quality assurance procedures are imperative to verify that the application functions as intended and adheres to the organization’s quality standards.

This phase may involve various types of testing, such as unit, integration, regression, and user acceptance testing (UAT), to ensure comprehensive coverage and readiness.

Deployment Execution

After comprehensive testing and validation, the deployment process begins. Depending on the organization’s practices, this may involve manual steps carried out by IT operations personnel or automated deployment pipelines managed by continuous integration and continuous deployment (CI/CD) tools.

Configuration Management

Effective management of configurations across diverse deployment environments, such as development, testing, staging, and production, is vital to maintain consistency and prevent configuration discrepancies. Configuration management tools may automate provisioning and configuration tasks for necessary infrastructure components.

Monitoring and Maintenance

Following deployment in the production environment, continuous monitoring and maintenance are essential to ensure the application’s availability, performance, and security. Monitoring tools track key metrics, identify anomalies, and facilitate real-time issue resolution. Regular maintenance tasks such as patching, updates, and security enhancements are conducted as needed to maintain system integrity.

Rollback and Recovery

Should deployment failures or unforeseen issues arise, the capability to revert to a previous application version or enact contingency measures is crucial to minimize downtime and mitigate risks. Robust rollback procedures and disaster recovery plans are essential components of this phase, ensuring rapid response and system resilience.

Documentation and Knowledge Sharing

Comprehensive documentation of the deployment process, configurations, and troubleshooting procedures is indispensable for fostering knowledge sharing and preserving institutional knowledge within the organization. This documentation not only ensures consistent practices but also supports the training and integration of new team members.

Practical Approaches to Deployment Challenges

Challenge 1: The deployment of the application succeeds on the test machine; however, it encounters a failure on the user’s computer due to a missing prerequisite

Some application packages come with built-in prerequisites, as designed by the vendor. However, others may require separate installations, such as VC Redist.


  1. Include the prerequisite in the installation package: This is a straightforward solution, especially when using tools like the PowerShell App Deploy Toolkit. You can add the prerequisite file to the package and include a simple installation command, ensuring rapid deployment.
  2. Create a separate prerequisite package: Alternatively, you can create a separate package for the prerequisite and add it as a dependency when deploying the main application. Over time, you can build an internal repository of prerequisite packages. When deploying the main application, if the prerequisite is already present on the machine, there’s no need to download it again. This reduces network usage and speeds up the deployment process.

It’s recommended to test application deployment on a clean machine to ensure all prerequisites are detected and included later on in the deployment.

Small prerequisites should be packaged separately and distributed as dependencies for the main application. These prerequisite packages can later be used by other packages in deployment.

Challenge 2: Auto-Update and Detection Failures – The application deployed successfully but after a while is reported as installation not detected.

When deploying an application, it’s crucial to define a detection method, commonly done by checking the uninstall registry path. For 64-bit applications, this path typically resides under `HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Windows\CurrentVersion\Uninstall\{appGUID}`, while for 32-bit applications, it’s under `HKEY_LOCAL_MACHINE\SOFTWARE\WOW6432\Microsoft\Windows\CurrentVersion\Uninstall\{appGUID}`, both followed by a `DisplayVersion` key with a value corresponding to the application version.

However, if the application’s auto-update feature remains enabled, the `DisplayVersion` will change with each vendor release. Consequently, the deployment system may interpret the updated version as not installed since it’s compared against an older version.


  1. Disable Auto-Update: Disable the auto-update feature during the packaging process. By maintaining a fixed detection method, the deployment system consistently recognizes the installed application.
  2. Modify Detection Method: If auto-update must remain enabled, altering the detection method from “equals” to “greater than” can address the issue. This adjustment ensures the application is detected as successfully installed as long as the version present on the machine meets the minimum requirement.

Clearly define and maintain the detection methods for installed applications to avoid misidentification.

Challenge 3: Deployment should remove any previous version of the application

If your package repository contains the prior version of the application package, it’s crucial to specify which package should replace it during deployment. This entails incorporating uninstall instructions for the previous package to ensure its removal before initiating the subsequent deployment.

However, scenarios may arise where the previous version isn’t packaged, complicating matters further, especially if the application was previously installed using both MSI and EXE installers, necessitating distinct uninstallation methods.


You can utilize the PowerShell App Deployment Toolkit code below in the pre-installation phase. This code searches for any application matching your specified application name, irrespective of whether it was installed as an EXE or MSI.

For non-MSI installations, adjustments may be required to accommodate different installer types such as Inno Setup, Wise, etc.

## Remove non-MSI versions

$AppsList = Get-InstalledApplication -Name “appname”

ForEach ($App in $AppsList) {

If ($App.UninstallString -and $App.UninstallString -inotlike “msiexec*”) {

$UninstallString = $App.UninstallString.Trim(‘”‘)

If (Test-Path -Path $UninstallString -PathType Leaf) {

           Execute-Process -Path $UninstallString -Parameters “/SP- /VERYSILENT /SUPPRESSMSGBOXES /NOCANCEL /NORESTART” -WindowStyle Hidden





## Remove previous versions of MSI

$AppsList = Get-InstalledApplication -Name “appname”

ForEach ($App in $AppsList) {

If (([version]”$($App.DisplayVersion)”).Major -lt ([version]”$($appVersion)”).Major) {

        Remove-MSIApplications -Name “appname”



Establish and document a standardized process for version management to ensure consistency across deployments.

When you create an application package update and increase versioning, make sure you follow our best practices described here.

EXTRA: Strategic Approaches to Minimize Disruptions During Forced Software Deployments

Deploying software efficiently while minimizing disruptions to user productivity requires careful planning and precise execution.

Below, we explore advanced techniques and best practices that go beyond the basic requirements to enhance the deployment process and mitigate potential disruptions effectively.

1. Optimal Timing for Installation

Select off-peak hours for installation, such as early mornings, late evenings, or lunch breaks, when users are least likely to be actively engaged with their computers. This helps to mitigate disruptions to productivity.

2. Advance Notification

Provide users with advanced notice regarding the upcoming software installation. Communicate the installation date, time, and expected duration, along with any necessary actions they may need to take, such as saving work or closing applications.

3. Implement Silent Installation

Whenever feasible, configure the software deployment to utilize silent or unattended installation modes. This enables the installation to proceed seamlessly without requiring user intervention, thereby minimizing interruptions

4. Suppress Reboot

Ensure that the deployment process suppresses any automatic system reboots that could disrupt users’ ongoing tasks. If a reboot is unavoidable, schedule it for the conclusion of the installation process and provide users with sufficient warning.

5. Leverage Deployment Tools for Deferred Installation

Employ deployment tools and systems equipped with features that allow scheduling or enable users to defer installation for a specified period. This grants users flexibility while ensuring the software is eventually deployed.

6. Establish a Rollback Plan

Have a contingency plan in place in the event of significant issues during deployment or if productivity is adversely affected. This plan may involve reverting to the previous software version or temporarily suspending the deployment until issues are resolved.

All these can be achieved using configuration management tools such as SCCM, Intune, and others. Here is a snapshot of some capabilities Intune deployment offers:


In summary, the dynamic evolution of application packaging and deployment presents both challenges and opportunities for organizations.

By addressing the key challenges discussed in this article and implementing practical solutions, businesses can streamline their deployment processes, enhance efficiency, and ensure successful application rollouts.

Moreover, strategic approaches to minimize disruptions during forced software deployments are essential for maintaining productivity and user satisfaction.

By combining technical expertise with strategic thinking, organizations can navigate these challenges successfully and thrive in the dynamic landscape of application deployment.

To Top

Pin It on Pinterest

Share This