The purpose of this paper is twofold: 1) to develop a high-resolution sea ice motion tracking system at the geospatial mesoscale (1-100 km2) and 2) to propose an algorithm that measures motion at close proximity to discontinuous regions. Here, we present a motion tracking system that computes differential motion at 400 m resolution and validate the accuracy/precision of this system via four studies. The first study measures the accuracy against displacements measured from in situ Global Positioning System (GPS) buoys deployed at the Sea-ice Experiment: Dynamic Nature of the Arctic (SEDNA) and the Surface HEat Budget of the Arctic Ocean (SHEBA) experiments. The estimates are found to be statistically comparable with GPS, with an average error of 361.9 and 600.6 m for the experiments, respectively. The second study compares the estimated displacements to those measured by the RADARSAT Geophysical Processing System. A precision error of 75.7 m is found between the two motion tracking systems. The third study uses intensity warping of randomly sampled measurements to evaluate discontinuous motion tracking. A one-tailed Wilcoxon signed rank test is used to validate these measurements at α = 0.01. Results from this paper prove that anisotropic smoothing produces significantly smaller errors at discontinuous locations (W = 4240 and p <; 0.001) over conventional isotropic smoothing. The fourth study compares displacements measured by anisotropic smoothing against manual measurements. This paper demonstrates an average reduction of the estimation error by 50 m with the use of anisotropic smoothing over the conventional isotropic smoothing.