The windowing technique has been a popular method to address the Y2K problem. In fact, about 80% of the systems used this technique. Unfortunately, the windowing technique is a temporary solution and windows will expire some time later. This paper proposes several approaches to address the expired window problem including modification and testing techniques. In software modification, ripple effect technique is used to locate all the necessary software elements need to be changed. In testing, both regression techniques and new test case generation techniques are proposed.