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Majority if not all times when I plug in my USB I want to use the USB Mass Storage functionality thus I was wondering there is a way to enable USB Mass Storage once a USB is connected.

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up vote 2 down vote accepted

Auto Mount Your SD Card should do that for you:

Automatically mount your SD card. Quit manually mounting your SD card every time you plug your phone into your computer.

I used that one one of my phones when I still connected it frequently via USB, and it did its job wonderfully. The app is available for free on the playstore, so nothing to lose :)

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