This work presents a model of single–machine scheduling problem. The machine is failure–prone and subject to random breakdowns. The processing time is a deterministic sequence that is randomly compressible, which may be from the introduction of new technology or addition of new equipment. Taking into account the cost for the random breakdowns and the random compressible processing time, our objective is to find the optimal scheduling policy to minimize an objective function. Under simple conditions, it is shown that the optimal sequence possesses aV-shape property