Been this way since at least Ubuntu 15.
Plug in your headphones, boot up your laptop. No sound. Speakers and headphones are disabled. Super annoying, you have to unplug and re-plug, and go through the stupid dialogue of "what are you trying to plug in?" which has no memory, and no defaults.
The "what are you trying to plug in" dialog is Ubuntu specific, it's not implemented by PulseAudio itself. If you want your last choice to be remembered, you'll need to talk to the Ubuntu UI people.
Maybe there's something in PulseAudio that could be improved regarding the default behaviour. Can you attach the output of "pactl list" after boot, when you have no audio? Please use the "Add an attachment" link (sometimes people paste long texts to the comment box, which makes following the discussion difficult).
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This bug has been migrated to freedesktop.org's GitLab instance and has been closed from further activity.
You can subscribe and participate further through the new bug through this link to our GitLab instance: https://gitlab.freedesktop.org/pulseaudio/pulseaudio/issues/193.