In OSX (Mountain Lion) Only allowing an application to open if a condition is met

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Is there any simple way to do this?

I basically want iTunes to not open if an external hard drive is not connected. This is essentially a user issue - as despite asking multiple times, my girlfriend will forget and open an audio or video file without the external HDD connected (where the iTunes library is kept) and so the usual rigamarole occurs... the media file will then try and add itself to the iTunes library, which can't be found, so it'll default back to it's position on the internal hard disk, and then when I come to use it, it'll try and consolidate it for me (which is nice), except it then decides it needs to organise it - and this takes about 6 hours due to the amount of music I have on there.

I've tried changing the internal (default) iTunes music folder path to an alias to the external one, but that starts throwing out some beastly errors once you get into the loop (when the alias is essentially a pointer to an invalid location).

Is Automator something that could be used? Sorry I'm not very pro with OS X I'm afraid.

Thanks, Duncan

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incidentnormal On

It seems a straightforward way to do this is just to move the iTunes.app onto the external hard drive, and replace iTunes.app in the Applications folder with an alias pointing to iTunes on the external HDD (called iTunes).

As iTunes is system protected, you'll need to change the permissions of iTunes.app to move it, which you can do via gui or terminal (sudo chmod...)

Simples.