If I m understanding the question correctly, MAIN.EXE gets a shortcut unless MIDDLEMAN.EXE is getting installed. In which case MIDDLEMAN.EXE gets the shortcut.

This is an odd problem in that the existance of a component changes the definition of another component. Still, it can be done. The way I would do it is create a component for MIDDLEMAN.EXE and define it s shortcut. Create another component for MAIN.EXE and don t define it s shortcut.

Then write a custom action that runs in the execute sequence in immeadiate execution that runs after file costing. Have it check to see if MIDDLEMAN.EXE is not installed and not being installed. If this is true, have a write a temporary row to the ShortCut table to define the ShortCut for MAIN.EXE.

From there you can let MSI handle the rest without the need for deferred custom actions to handle servicing the shortcut.

Still, I can t help wondering if this couldn t be simplified by changing the design of the application. Basically you are trying to do dependency injection at the EXE level and it would be easier to accomplish this at the DLL level. In otherwords:

MAIN.EXE with ShortCut Optional DLL

The MAIN.EXE is always called but he will behave differently when Optional.DLL is present.

Assuming the default component is included in the installation, you can probably use a component condition for your extra component. You can then make sure that this extra component is installed only if the other component isn t, i.e. they become mutually exclusive. This will avoid any messing about with features that would make your Custom dialog much more complicated.

@Stephen: I can t see how you can avoid using features since only features are visible to the user in the GUI and hence allows the user to specify what to install?

I generally don t like this kind of solution since it doesn t validate according to internal consistency checkers for MSI files, but you can install the EXE in one component, and then have two components each with different shortcuts that you condition to be mutually exclusive. You then attach the customized shortcut component to the feature which triggers the custom shortcuts to be installed. The feature must be set visible in the GUI. The shortcuts must be non-advertised since they are in components without files. You may need to set the transient flag on the shortcut components to allow removal / addition of the right component for maintenance installs. Transient components have their component-conditions re-evaluated during maintenance installs to check if the conditions specified for them will trigger removal / addition.