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I'll spare you the long story, but I'd like to know if there's any way to force my computer to output Mono sound, but only when a specific set of headphones are plugged in (namely, my earbuds), but NOT when I plug in other peripherals such as my 2.1 speaker system, or when just using the built-in speakers of the laptop.

Is there any way to be this specific?

Using Windows 7 on Alienware M17x R2

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Yes! Buy a stereo to mono adapter for the earbuds. There is no way for the jack to differentiate between devices because they are not bluetooth.

something like this: http://www.radioshack.com/product/index.jsp?productId=2062469&locale=en_US