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My headphones plug broke into two pieces, one with me and the other inside the jack in my laptop. Now, I wanted to ask if there is any way to use a usb headphone and use both the devices at the same time since my system still recognizes the half jack inside?

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Generally you cannot output all system sounds to both devices at the same time. You can however select what audio producing programs go to what audio device. Right click on the sound icon in the tray and bring up the "mixer". From there you can select which audio device to use.

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