You could get a more definitive answer if you posted your crv file. The reason your file cut as it did is that the size of the bit is too big for the carving. It won't fit into the missed areas. If you're using the pocket toolpath, you can check the box 'Show Advanced Toolpath Options'. With this option checked , you can check 'Use Larger Area Clearance Tool'. This will allow you to use your current bit as a clearance bit, then switch to a tiny bit for the detail work.