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Despite some claims... the physical hardware should be able to do it... but I don't know if OSX can do that.

http://www.behardware.com/articles/555-3/intel-high-definition-dio.html

The HDA also introduced (and imposes) Jack Sensing and Jack Retasking technology. With Jack Sensing the controller identifies a mini-jack plug when inserted. The principle is simple. Each mini-jack input and output has a switch, which is open when empty and closed when a jack plug is inserted. The system tells the driver, which then asks the user which type of media has been connected to the audio chipset; speakers, headphone, recording source, microphone, etc.

Jack Retasking then comes into effect. This technology assigns various tasks to an input or output. So it’s possible to transform lines and micro inputs to additional outputs, for example, for a 7.1 system. Or you can plug in two microphones, one on the line input and one on the micro input, because all entries with HDA codecs can theoretically benefit from microphone pre-amplification. We will see later that this isn’t necessarily true and that some HDA systems restrict Jack Retasking capabilities to the front panel. These ports are generally meant for stereo output and line input, which can be configured according to your needs.

It makes sense when you realize that the Intel solution is targeted for basic computers with normal inputs and outputs as well as 7.1 systems where some of the jacks need to be remapped ( dynamically? ) to allow for rear channel operation.
 
bit off topic, but

does anyone know of a way to have the built-in speakers and external jack outputing sound at the same time?
 
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