Plugged in headphones but sound from speakers

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Or perhaps you remember how it once use to be when it just worked automatically?

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But then 30 minutes later you want to listen to your audio through your speakers and you have to go through the process again? So you go to your Premiere Pro Preferences and then to Audio Hardware and change your default Audio Output to External Headphones. So you want to edit in Premiere Pro with your headphones plugged in, but after you plug them in the audio still plays out of your speakers?