You can certainly do that, but it's going to be up to the app in question if it supports multiple audio endpoints at once. Apps typically don't do any special coding and just use the default endpoint.
Dual audio connectivity
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Anonymous
Does anyone know if you are able to use a wired pair of headphones (via headset jack) and a Bluetooth headset simultaneously? would like to be able to share audio on trips so we can watch movies on the plane.
Surface | Surface Headphones | Setup and pairing | Windows
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Anonymous
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Anonymous
2015-10-25T19:01:56+00:00 I'm just watching a movie on iTunes and or Flixter there is no setting for audio output. I plugged in a iPhone speakers while I was using the Bluetooth and you couldn't hear through the iPhone headphones.
Kevin