Abstract-In this study, we experimentally investigated the process leading to fracture in tofu grasping by deformable fingertips filled with a fluid. In our previous papers [1, 2], we developed deformable fingertips using a rubber bag filled with a viscoelastic fluid, and presented a strategy for delicate tofu grasping without any advance knowledge about fracture. However, the predication point was close to fracture, and the prediction was then still a gamble. In order to realize fracture prediction at an earlier stage, we examined the process leading to fracture when pushing tofu by the deformable fingertips. The stiffness of the fingertips can be controlled with the pressure of the fluid inside the fingertips. The pushing force and fluid pressure were examined for different levels of stiffness of the fingertips. The main findings and contributions are as follows. 1) The convergence of the ratio of the contact force to fluid pressure gives an indication of dent occurrence. This convergence could be seen when fingertip rubber bag was not filled (low stiffness). 2) It was easier for a dent to occur when the fingertip rubber bag was not filled than when it was filled (high stiffness). 3) Changes in the rate of increase of the fluid pressure as the tofu was pushed were repeatedly observed. We defined this as a phase change and present a method for detecting such changes. The phase change points were detected by comparing the fitting accuracies of different approximation models. 4) The last and second to the last phase changes before fracture were detected by detecting the first phase change (after the convergence of the rate of the contact force to fluid pressure if the fingertip bag was not completely filled). The detected points can be regarded as alert points indicating a fracture risk that is not close to the fracture point.