update: I should have qualified my earlier reply with…
As an alternative to relying on sheetcam to recognize a shape as a perfect circle and thus start the leadin in the middle per the option selection, you can experiment with these techniques…
Experiment with adjusting ‘Start point tool clearance’, see this post - Tight corners and start point clearance %
2nd, consider putting all these irregular small shapes into a separate layer and cut them with a very short or long leadin shape of your choice.
3rd, if its just an occasional shape behaving like this, you can edit individual start points by using menu Mode / ‘Edit start points’, then right click on the start point and select Properties, adjust the leadin as you see fit.