Abstract: The present invention generally provides a system and method for stiffening a cutting tool assembly used in cutting laterally relative to a wellbore axis to reduce stresses and cyclical bending of the cutting tool assembly during cutting. The system includes a cutting tool attached to a shaft such as an output shaft of a motor or a drill string. A sleeve is disposed in an annular space, known as a box relief, defined between the shaft and a peripheral wall of the cutting tool. The sleeve is preferably fixed in the annular space by a sleeve ring surrounding a recess in the shaft, but can be coupled to the peripheral wall and/or shaft by, for example, a threaded engagement.