I also get this happening from time to time and don't know where the door or window disappears to. You can try pressing 'U' to Update your PC display list as the door may already be there but just not re-displayed after using Re-associate? Another "trick" to re-associate doors/windows is to use the Edit/Cut then Edit/paste to place the entity back into the wall.
Use this forum to ask questions about DataCAD 22 and DataCAD LT 22.
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