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I have a cube that I am cutting two holes into. I put in a cylinder and duplicated the cylinder. I then made a boolean modifier of the first one and it worked. The second one doesn't. I've recalculated normals and not sure where to go from here. (2nd day of blender newb).

My blend file:

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Look at the object you're using as boolean object, there are 2 separate cylinders, you need to bridge them otherwise it won't boolean the cube:

enter image description here

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