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One option would be to configure the package to run as the installed user. However, depending on your user permissions, that may present some problems. I'm not super familiar with the nircmd infobox command, but perhaps it has an option to send the box to the correct user session? That might let you get the prompt to appear?
This does work as expected when running the package as the logged in user. Not super helpful for package installation however as our end users do not have administrator privileges. We could of course setup a package bundle with a package to do all of the necessary checks before moving to the actual install package run as local system. More complicated than we'd like but wouldn't often be necessary. That said, it would be nice if there were built in functionality to prompt or query the end user during a deployment.
Thank you for your help!