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Is it possible to use analog headphones (in the regular headphone jack area) and USB headphones at once on a windows computer? Every time we plug both in the USB headphones override the analog headphone and sound is only heard from the USB headphones.

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what you're using the headphones for, and what purpose would help get a more detailed answer. – Journeyman Geek Aug 19 '11 at 2:48

I would say the USB headphones have their own 'sound card' built in and when you plug them in a new audio device is created in Windows.

Unfortunately Windows can't play the same audio to two different devices simultaneously (but you can switch between them). Also, some applications will let you choose which device the audio is played on.

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What you are looking for is multi zone audio, which are software and hardware solutions that output to multiple soundcards. I don't have any recommendations as I've never used them. But I thought knowing what to look for would would help you out.

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