Anagram Headphone Output vs XLR Output Tone Difference

Hi all, I've a weird issue with my Anagram bass pedal. I use IEM (KZ) and overhead headphones (Beyerdynamics DT 770 Pro) to dial a tone and practice. I can dial in a highly overdriven tone, and it sounds perfect in the phone output.

When I connect it to my DAW, and listen through the earphone out of my sound card, still pretty solid.

But when I run it through a PA, amp or my reference monitors (KRK Rockit 5), most of the overdrive is gone and it is very hard to distinguish if it is a clean tone or not!

This happened in rehersals as well where I connect my Anagram through a mixer to the PA. I thought it was a frequency issue with my monitors, but seems like it is not. Has anyone experienced something like this?