Playback output: external speakers and headphones

I’m scoured and tried everything I know or could find to fix this issue, but I can’t seem to figure out how to playback files thru headphones or an external speaker on my Mac.
Can anyone help, please?

Windows guy here. On some machines, just plugging in the headphones re-routes audio from the internal speakers to the headphones.

On others, plug in the headphones first, then startup Audacity (or do Transport > Rescan Audio Devices), then select the headphones from the Audio Setup drop-down list.

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