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I am currently running the following:

4.15.0-46-generic GNU/Linux
Distributor ID: LinuxMint
Release:    19.1
Codename:   tessa

I have my headphones plugged into their dedicated port, however, I also have stereo speakers plugged into the back of my motherboard which I use as well. Currently, to use either of them I have to physically unplug my headphones to use my stereo speakers.

My question is: can I switch between them in the Operating System itself?

When I plug my headphones in, the Line-out audio device gets replaced by my headphones. In windows, I was given both options simultaneously, making switching between them a bit less of a hassle.

Headphones as output device Line out as output device

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You should consider using paprefs.

You need to install it:

$ sudo apt install paprefs

Then, once you run it, go to the Tab "Simultaneous Output" and tick the following box:

Simultaneous Outputs

A newly output is created that you need to select in the tab "Output" from the PulseAudio preferences, which broadcast the sound on every output:

select new output

This should do the trick.

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