The estimation of the network traffic state, its likely short-term evolution, the prediction of the expected travel times in a network, and the role that mobility patterns play in transport modeling is usually based on dynamic traffic models, whose main input is a dynamic origin–destination (OD) matrix that describes the time dependencies of travel patterns; this is one of the reasons that have fostered large amounts of research on the topic of estimating OD matrices from the available traffic information. The complexity of the problem, its underdetermination, and the many alternatives that it offers are other reasons that make it an appealing research topic. The availability of new traffic data measurements that were prompted by the pervasive penetration of information and communications technology (ICT) applications offers new research opportunities. This study focused on GPS tracking data and explored two alternative modeling approaches regarding how to account for this new information to solve the dynamic origin–destination matrix estimation (DODME) problem, either including it as an additional term in the formulation model or using it in a data-driven modeling method to propose new model formulations. Complementarily, independently of the approach used, a key aspect is the quality of the estimated OD, which, as recent research has made evident, is not well measured by the conventional indicators. This study also explored this problem for the proposed approaches by conducting synthetic computational experiments to control and understand the process