Hi Andy, when you're doing the flow to create your text you should position the text so it will punch some distance through the surface of the cylinder rather than just skimming right along the cylinder's surface.
Objects that have coincident surfaces where the surface areas skim over top of each other are much more difficult to boolean, the intersector will try to find an intersection between the 2 surfaces that are close to being coincident but have some very small differences between them.
You can sometimes use skimming surfaces ok if they are very exact like 2 planes exactly on the same plane.
- Michael
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