Could have been a couple of things...
1) The audio output assignments.
2) The headphone cueing.
Can you post a screenshot of the audio config page of the preferences?
I had an issue over the weekend I am hoping you can help me with. Not sure if it was a glitch or something I did wrong. I'm using the DDJ 1000, 2012 Macbook Pro with SSD and 16gig ram and MacOS 10.13.6 High Sierra. Also 5.4.0 official release.
The problem, not matter what I did, the song going though the master was coming through my headphones. I'm not a rookie so I understand how the cue/master works. I dug through the software and settings to find the issue but nothing I did resolved the issue. Maybe I missed something? Yes, I looked through the mixer section of Rekordbox as well. It definitely wasn't the song preview either.
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Could have been a couple of things...
1) The audio output assignments.
2) The headphone cueing.
Can you post a screenshot of the audio config page of the preferences?