Projects are rarely executed exactly as planned. Often, the actual durations of a project’s activities differ from the planned ones, resulting in costs stemming from the inaccurate estimation of the activities’ completion dates. While monitoring the project at various inspection points is pricy, it can lead to better estimation of the project completion time, hence saving on costs. Nonetheless, identifying the optimal inspection points is a difficult task, as it requires evaluating a large number of the project’s path options, even for small-scale projects. This paper proposes an analytical method for identifying the optimal project inspection points by using Information Theory measures. We search for monitoring (inspection) points that can maximize the information about the estimated project’s duration or completion time. The proposed methodology is based on a simulation-optimization scheme using a Monte Carlo engine that simulates potential activities’ durations. An exhaustive search is performed of all possible control points to find those with the highest expected information gain on the project duration. The proposed algorithm’s complexity is not affected the number of activities, and can address large projects with hundreds or thousands of activities. Numerical experimentation and analysis of various parameters are presented.