Maybe i understand you wrong, because my English is not the best:

You want to make sure, that your files are ensured before your service 
running up?
You can use a simple require to make that sure

service { 'app1':
     ...
     require => [ File['C:/Program Files (x86)/application/app1.exe'] ],
}


if you want your service restarts when your file is changed during the 
process (helpful sometimes for .ini or config files)
you can you "subscribe" instead of "require". This to metatypes works with 
the most resources in puppet. For example, if you want that some 
WindowsFeatures and specific applications are installed, before the 
installation of another package starts, you can handle this on this way.


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