I have a pair of headphones connected to my desktop's back panel and a headset connected to the front panel. I used to play sound over both outputs, but this suddenly stopped working this week.

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Apparently, (perhaps through some update) "jack sensing" got turned on, which disables the back panel as soon as you connect something to your front panel audio jack.

To disable this feature, I used alsamixer (use the arrow keys to navigate right to "auto mute", and disable with the up key). For some reason the corresponding checkbox in the gnome-alsamixer did nothing for me.