Knowledge on the behavior of lubricant trapped in a surface pocket is important for improving metal forming technology, since the trapped lubricant affects friction and surface finishing. The permeation phenomena at higher reduction in height were quantitatively observed during the upsetting of cylinders with a central conical dent using the new fluorescence direct observation apparatus developed by the authors. Moreover, the permeation phenomena were estimated using a rigid-plastic finite element analysis model incorporating the compressibility of the lubricant. From the experimental results, it was quantitatively observed that over a reduction in height of 37%, the outline of the central conical dent became blurred, and the lubricant trapped within the conical dent permeated into the peripheral real contact area. It was also quantitatively observed that the volume of the lubricant trapped within the conical dent decreased gradually and abruptly with increasing reduction in height up to and above 36%, respectively. From the numerical results, it was estimated that the trapped lubricant permeated when the hydrostatic pressure generated within the lubricant pocket exceeded the die pressure at higher reduction in height.