By 'headset' do you mean the quill stem? The bolt that secures the wedge at the bottom of a quill stem should be loose enough to slide the stem into the steer tube. If it got tightened for some reason while out, this may explain why it won't go back in easily. The 'top screw' on a threaded headset only adjusts the headset, and should have no effect on inserting the quill stem.