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I've had this issue with Ubuntu starting from 16.04 and it still persists in Ubuntu 20.04.

Here's the problem: whenever I plug in my headphones, it asks me to select an audio device (it gives me three options: headphones, headset and microphone), and even if I don't select one and click Esc, the headphones still work, so that tells me this prompt might not be necessary but I couldn't find any way to disable it.

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As someone pointed out in the comments, there's a GNOME extension for this and after searching a bit, I found it in this answer, and the extension is available here