Intersecting Push/Pull

I have already made a hole via push/pull on one axis. I’m now trying to do the same on a different axis but which intersects the first hole. I need it to go through the fist hole. Can someone tell me why the push/pull stops when it hits the edge of the first hole?

Pushpull does a flat extrusion. It can’t handle curved surfaces. You need to create a cutting cylinder separately, move it into place, and then use either intersect faces with or if on Pro the solid tools. If the part is small you will probably need to use the “Dave method” to avoid losing small features (search the forum).

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The short answer is that Push/Pull can’t move past a curved surface. If you tap the Option key (Mac) you can force Push/Pull past the curve. Or you can use a plugin called Joint Push/Pull from Fredo6.
But if you want two intersecting holes, you’re better off using the Intersect Faces routine. Drill one hole as you normally would. Make the part with the hole a component. Close the component for editing. Now draw a cylinder whose diameter is the same as the second hole you want. the length of the cylinder is unimportant, as long as it will pass completely through the component you want to drill. Position the cylinder where you want it in the component. Cut it from the model, open the component, and go to Edit>paste in place. Now, select all, right-click, and choose Intersect Faces>with selection. This combines the two shapes. Erase the waste to reveal the hole.
It takes longer to write this explanation than to do it in SketchUp.