How to handle package install failure when package is already installed?

How to handle package install failure when package is already installed?

New to EC and using a Gemini for a lot of guidance. 

I have a package I'm deploying. The package installs successfully when it's a new install but in subsequent checkins it shows as failed. I assume because the package has already been installed. The reason given is "Installation Failed - User cancelled installation." but it's a silent install so the user is not cancelling install. I've tested on a few machines already and confirmed that user gets no prompt. When I uninstall the package and it runs again it's successful once and then, again, subsequent check-ins give the error "Installation Failed - User cancelled installation".

What is the best approach to handle this? I tried some powershell scripts as part of pre-deployment to return 0 or 1 but couldn't get that to work. Not sure if that is the best approach and looking for some suggestions and guidance.

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