If you are not familiar with the loopback feature of Audicity, I'll tell you that it happens completely "in the box". It captures what audio is being sent to the dac, but it has nothing to do with the dac itself. It's useful because it lets you see what your system is sending the dac after all effects and mixing took place.
Theoretically I could test what actual analog signal is coming out of the dac to see if there is any intersample over issues, but that would involve analog signals and ADCs and the result would be a lot dirtier and maybe even less revealing. I don't have the kind of measurement equipment Amir has to go to such low resolutions.
As for why low-cut creates clipping, I concocted this test:
I took a complex signal (two unrelated frequencies), and add a small bump that just pushes the signal to clipping at a specific point. then I added the key ingredient, which is asymmetric distortion – basically, the positive goes over 0dbfs while the negative doesn't. this is actually a common type of distortion used in tubes. After that, I mixed in a 5hz sinewave, and aligned the signals such that the a negative peak of the low tone will coincide with the clipping samples of the complex signal.
So this is how the signal looks with will all of them mixed together:
View attachment 76411
And now if I add a sharp high pass filter at 20hz, we get this:
View attachment 76412
Clipping!