The undrained shear behavior of soils with progress of shear displacement is essential to the understanding of liquefied slope failures with long travel distance. In this paper, using a newly developed ring shear apparatus, a series of ring-shear tests were conducted on a silty sand to examine the undrained behavior of sand subjected to long shear displacement. Based on the test results, the undrained shear behavior of sands with a wide range of densities is discussed. A very low effective stress corresponding to liquefaction was observed at the steady state in all of the tests on loose, medium, as well as dense sand. The effects of stress state and shear history on the undrained shear behavior were examined by performing tests on a sample with different initial stress states and shearing the same specimen repeatedly (three times) at each initial stress state. The tests at different initial stress states proved that the initial stress state has an influence on static liquefaction resistance but has no effect on the steady-state shear strength. Repeated shear tests on the same specimen showed that with increasing shear times, both the peak shear strength and the steady-state shear strength for each specimen became greater. Detailed examination of the shear deformation revealed that the liquefaction phenomena in ring shear tests are localized in the shear zone, irrespective of the initial state of the sand. Grain crushing within the shear zone was examined. Finally, it was found that there was an optimal density at which the undrained brittleness index had a minimum value; meanwhile, the undrained brittleness index became greater with increasing initial normal and shear stresses, but decreased with shear times. These findings offer some basic understanding in assessing the postfailure mobility in landslides.