Data assimilation systems (DAS) are difficult to evaluate in part because there is limited independent data to use for verification of performance. In an Observing System Simulation Experiment (OSSE), the full true state is known exactly, in the form of the Nature Run. The availability of this truth allows the investigation of DAS characteristics in the OSSE framework that are not quantifiable in the real world. The synthetic observations can also be manipulated to test configurations that range from idealized to highly realistic. A sampling of OSSE investigations into the behavior of 3DVar and 4DEnVar DAS and adjoint observation impact estimation tools will be illustrated using the National Aeronautics and Space Administration Global Modeling and Assimilation Office (NASA/GMAO) OSSE.