Handling Windows Defender SmartScreen Warnings during Agentless MSI Installation

Overview

When downloading and installing a new release of the Cloudamize Agentless MSI via the double-click (GUI) method, users may encounter a blue "Windows protected your PC" notification.
This is a standard behaviour of Microsoft Defender SmartScreen. It occurs because SmartScreen uses a reputation-based system, every new version of an MSI is considered "unrecognized" until it has been installed a few hundred times globally.

How to Proceed (Manual Installation)

If you are installing the MSI by double-clicking the file and see the SmartScreen prompt, please follow these steps:

Click "More info": This link is located in the text description of the blue window.
Verify Publisher: Confirm that the publisher is listed as "Cloudamize Holdings, Inc".
Run anyway: Click the button at the bottom of the window to proceed with the installation.

Impact on Automated & Command Line Deployments

It is important to note that this warning is specific to the Windows Shell (double-clicking the file).

Command Line (CLI): This screen will not appear and will not interrupt installations launched via the command line or terminal.
Network Drives: If the MSI is copied via a network drive and launched via double-click, the warning may or may not appear depending on your local intranet security settings.

Why is there no workaround?

Microsoft design dictates that reputation is tied to the specific file hash of each new release. Because Cloudamize prioritizes frequent updates and security enhancements, each new MSI must "earn" its reputation through the first few hundred manual installs. Per Microsoft’s official documentation, the only way to bypass this entirely is through the Microsoft Store, which is not applicable for enterprise agent deployments.

Technical Reference

For more details on how Microsoft calculates and applies application reputation, please see the official Microsoft documentation:

https://learn.microsoft.com/en-us/windows/apps/package-and-deploy/smartscreen-reputation

Note to Administrators: If your security policy prevents users from clicking "Run anyway," we recommend installing the Agentless data collector via Command Line method.

If you have any questions or need assistance, please reach out to our helpdesk at helpdesk@cloudamize.com