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Blender

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  • $\begingroup$ Thanks for the answer, so the only solution would be to apply the Boolean modifier first and then apply subsurf afterwards? $\endgroup$ Commented Apr 6, 2021 at 13:56
  • $\begingroup$ I wouldn't say it was the only solution but it is the only one I can think of. Apply the boolean then mark the circle boundaries as edges and the the subdivision surface would be happier. It might be easier to model one quarter of your model though and let the mirror or array modifier handle the rest. $\endgroup$ Commented Apr 6, 2021 at 15:10