The high accuracy of log positioning and the stability of saw blades in breakdown machinery in modern sawmills have reduced the need to add margins for sawing variations. Oversize green sawing dimensions are still needed, but mainly to allow for drying shrinkage. This has put a new focus on better adapting green sawing dimensions to the shrinkage behavior of wood. In this study, a method for optimization of green sawing dimensions using stochastic simulation is presented. Normal distributions were generated for planed dry dimensions, kerf width, and target moisture content. The minimum share of boards exceeding the specified dry dimensions was decided, and deformations in boards from all positions in the cross section in a number of logs were simulated. The simulated shrinkage allowance from stochastic simulations was compared to experimental results from an industry test and to finite element results based on material data for Norway spruce. The results showed that the green width of the sawn boards should increase when the number of boards in the center yield increases. The green thickness of boards should be thinner for center boards and outer boards than for inner boards.