Deploying Poorly Packaged Applications with PowerShell and SCCM

In real-world environments, not all enterprise software comes with a proper installer.

Recently, I had to deploy a legacy DLP agent that had:

• multiple versions across endpoints
• different ProductCodes
• the same display name
• limited documentation
• and no reliable upgrade path

Trying to handle this using standard logic in Microsoft SCCM (multiple detection rules, MSI-based upgrades, etc.) quickly became messy.

The Approach

Instead of relying on SCCM alone, I moved the logic into a PowerShell-based installer.

The idea is simple:

• Detect if the application is installed
• Check the installed version (via ProductCode)
• Remove anything that doesn’t match the target version
• Install the correct version with required parameters

In SCCM, the detection method stays clean — it only checks for the new version.

Why This Works Better

• No need for multiple detection rules
• No leftover versions after upgrades
• Full control over install/uninstall logic
• Works even with poorly packaged or legacy software

Key Idea

Instead of trying to model every scenario inside SCCM, centralize all logic in a script.

This makes deployments more predictable and much easier to maintain.

Full Breakdown

I wrote a detailed step-by-step guide here (including SCCM setup and scripts):

👉 https://www.hiddenobelisk.com/how-to-deploy-poorly-packaged-applications-using-powershell-and-microsoft-sccm/