This paper presents a new strategy for determining an optimum position of monitoring point and criteria with which judgment is made if the settlement values at the point are critical or not for a significant structure adjacent to tunnel construction. The position and criteria are differently given to each structure by considering its geometry and exact position. It is unlikely to the conventional monitoring scheme undertaken by a fixed criterion applied at certain monitoring points that are also intuitively placed. The strategy proposed is based on an iterative scheme by incorporating the so-called Intelligent Tunneling Information System (ITIS). Details of the iterative procedure are described with an illustrative example. In the example, the settlement criteria at three different damage levels are given at an optimum monitoring point.