Help figuring out cuts

hey guys I’m doing a project with an eagle and deer and a cabin with titles. i wanted the deer and eagle done on clean out a pocket i have it set at about 3/16 deep to cut. but the eagle and deer disappears on cut out a pocket but reapears when i click on cut on shape path. also noticed if i add the 60 degree bit as a 2nd bit it will reapesr but i don’t want to haft to switch bits what should i do?

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