Not cutting first pass -Shapeoko 3

I am having trouble with my machine never cutting on the first pass. I have used both a probe and paper method of zeroing the z axis but neither address the issue. I have start depth set to stock top and bottom to .121 for 1/8" BB which is a little thinner than 1/8.
Thoughts? I have problem since day 1 and I wonder if I am doing something wrong.

What software? Did you set your work zero in your design to the bottom of the workpiece?

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Is the material entirely flat? I have that issue quite often.

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