Subject Group from Another Group

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I’d like to be able to subject one group of shapes from another group of shapes, but unfortunately the option is never available. Any way to pull this off?

This is the original artwork and goal:
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In the first picture, you show the skate vectors as a group (dot dot dash). Is the “bone” vector art as well? Is it a group. If yes, select both and the ‘Boolean’ tools should light up and become available. Is this not working for you?

Yes, I have both the skate as a group, and the bones as a group, but when I select both the options disable on the menu.

Post the file so I can take a look.

I started over and now it is subtracting. If I can’t figure it out in the next 15 minutes, I’ll post it. I thought it should work, but for some reason what I had was not. A fresh start and it’s giving me options again.

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I figured it out! Not sure what I did different, but it worked!

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Well, it’s happening again. If it works for others, it must be my order or operations or something. Advice and suggestions welcome!
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Map Merge Example.lbrn (2.7 MB)

Click Edit > Select open shapes.

None of those will work with a boolean operation, because booleans are combining the enclosed area of a shape in the described ways, and simple lines do not have area.