The pocket tool struggles with complicated geometry.
The way around it is to split the shape into simpler shapes.

1) apply the boundary to the shape, hold down CTRL when clicking with the pocket tool.
2) simplify the shape by adding lines to create simpler areas.
3) add zigzags to the simple areas, hodl down SHIFT while clicking with the pocket tool.
4) if your stepover% is smaller than 50% then remove the split lines
if larger than 50%, convert the split lines into fold cuts at the same depth as the pocket lines.

See it in action here