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I posted this a few weeks ago but never got an answer that seemed to work for me so I am posting it again, hoping someone else may see it and have an answer.

How can I add stroke to an object or trutype font and have the cutter cut the outer stroke without cutting the shape of the smaller part also (the shape before the stroke is added)?
 

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When you apply an outline (stroke), under the Arrange Menu is "Convert Outline to Object", which will make that outline into its own vector object. Always save your work before doing this. I've had instances where it wanted to take an hour to convert, and also had it just flat out crash, it depends a lot on the complexity of the object.
 
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