This is how I configure OBS on my Macbook Air M1 to stream and record desktop system sounds while monitoring with external headphones.
1. Install BlackHole 2ch… https://existential.audio/blackhole/
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2. In Audio MIDI Setup, set up Multi-Output Device. If Multi-Output Device is not there, click the + button to add.
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3. In System Preferences – Sound, select Blackhole as Sound Output
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4. In OBS Audio Setting, set Desktop Audio to BlackHole and Monitoring Device to External Headphones.
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5. In OBS Audio Mixer Advanced Audio Properties, set Audio Monitoring to Monitor and Output for both Desktop Audio and Mic. Toggle this if there is no sound.
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Let me know if this works for you.
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~ Adrian Lee