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@gbj_tester
Maybe somebody did the bolt up tight when the stem was out of the frame, permanently deforming the two legs at the bottom. Measure it at the solid top section of the quill and at the bottom and see how much difference there is. If it's deformed, you could try putting a jubilee clip around it about 5mm up from the bottom, tighten it up until the stem fits into the steerer tube and then take the clip off once you've got the first 5mm of the quill into the steerer