From Sheldon Brown

"Note: Steerers are butted at the bottom, so the hole in the steerer is constant-diameter until near the bottom, then the walls taper inward in the butted section.
It is vitally important that the stem extender (or stem) is not inserted so far that the wedge is installed where the steerer is narrowing, or it could come loose unpredictably.

When this happens, only the edge/corner of the quill or wedge contacts the steerer, and it is trying to "grab" a slanted surface.

This is sometimes a problem on smaller frames if you try to insert the stem or a stem riser too far down into the steerer."