Why I cannot intersect faces?

Why I cannot to intersect faces so I could to push pull the oval shape into the yellow “wall”? I tried to select the oval shape and then intersect with Model or with context. Then I want to select the yellow face which should be intersected, but it is not intersected still.

test.skp (60.6 KB)

Both shapes need to be seperate groups or not grouped at all.
Alternatively you can try ‘Drape Tool’.

The first comment by @filibis is where your problem lies. See simple screencast below where I explode the group to make all the geometry “equal” before isolating inner shape and pushing through.

Related to this …
I am experiencing mystery problems when intersecting faces with model.

Consider a flat vertical plane being intersected with a house-wall in order to
“cut out” the windows and doors in order to skin-over the internal structure.

I always make sure that the plane is slightly “inside” the surface geometry
to ensure it is truly intersected. Coplanar geometry sometimes does and sometimes does not get intersected properly.

I observe the rectangle geometry being superimposed on the vertical plane, but when I go to “cut out” the opening faces, some of them are not separated from the rest of the whole plane. There are apparent leaks or non-coplanarities.

Sometimes I will try to bisect/triangulate the leaky openings, deleting those faces which are separated and that process can generate quite a convoluted and non-intuitive mess.
Sometimes I just draw another rectangle over the intersection-generated rectangle.
Sometimes that solves the problem for that particular opening, other times it does not.
I have resorted to just creating yet another new plane on the face or the intersected plane, manually re-drawing the openings inferenced to the intersected openings and abandoning the intersected plane/geometry.

Anyone run into this ? And have a workaround?
There is probably some addin to enforce coplanarity of selected geometry…
This has to be a bug.

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