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User Experience during application deployment ( required / available)

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Looking for some help here..

We have an application (not a package) that is configured to run 'whether or not a user is logged on'. 

The application has to close the previous version if it is open, as such we feed the run the msi with a /Q parameter. In the case where the application is open, the user is not asked to answer anything. However, if the application IS open, we prompt the user to confirm that it is ok to close the application and continue. 

When this application is deployed as required, and the user is not logged on - everything runs smoothly. Same for when the user is logged on but the application is NOT open.

However - when the user has the application open, the application installation begins, but the installation (and required popup message) are not visible to the user as the 'allow users to interact with this application' checkbox could not be checked. 

(Side note, if you deploy this as available and even though the application is configured to be hidden, it runs visible - is this a bug?)

So the question is:

How do you deploy an application that should run whether or not the user is logged on, but when they are logged on it should allow them to interact with the application?

Will


Will


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