How does the clipping indicator work?

Does the clipping indicator operation depend at all on the downstream devices I’m using? Or is it triggered solely by the DSP and volume levels controlled in/by the Roon Core?

To put it another way: Suppose my amp has an LED clipping indicator on its front panel. Should I expect a close correlation between the amp’s clipping indicator and Roon’s clipping indicator?

Roon’s clipping indicator is solely about digital clipping occurring in the core (DSP actions). Read: DSP Engine: Headroom Management

No, this is completely unrelated.

I turned headroom management down/off (with volume leveling also off) and the system sounds a little better. With upsampling the clipping indicator now goes off on some tracks (until I give it -2 dB or more headroom.) But, if I wasn’t looking at the clipping indicator I would not know it is clipping. So should I care about the indicator?

From the above linked article:

Headroom Management is at the top of the list because it’s one of the most important things to pay attention to in Roon’s DSP Engine. If things don’t sound right, one of the first things you should do is make sure that the signal isn’t clipping.

So if you don’t hear anything unusual, you can ignore him – but don’t turn him off. Should at some day something sound odd, look at it again.

I’m thinking, with upsampling and without headroom management (or vol leveling) certain frequencies do trigger the clipping indicator, but apparently they are outside my hearing range or the clipping is very short in duration.

I had done some DSP to manage the speakers in my office that were off center. One day I noticed the left speaker had static. I thought the tweeter was going out. I went so far as to order a replacement driver for the speaker. Then I noticed the clipping indicator was lighting up. I put in a touch more head room and the speaker noise went away. Long story short, now I have a spare tweeter. Roon is your friend.