The typical preparation plant producing coal for the utility market targets a relative separation density in the plant of around 1.60 whereas plants generating metallurgical coal use relative cut point density values approaching 1.50. In some cases, achieving the specified coal quality requires operating at lower cut point values, which results in a significant loss of valuable coal. In these situations, a middlings stream can be produced using a secondary separator or a three-product unit, which would allow crushing of the middlings for liberation purposes and re-introduction into the plant feed. In this manner, higher quality coal can be produced while maximizing plant yield. A detailed laboratory analysis was conducted to study the liberation characteristics resulting from the crushing of middlings at different top sizes. The experimental data were later used as input for modeling and simulation of plant flowsheet in LIMN. Simulations were run for several regrinding cases. The results of the current study investigating the economic benefits of middlings liberation and re-treatment are presented and discussed in this thesis. Improvement up to 6% in plant yield with 16-21% reduction in ash and 14-18% sulfur reductions can be achieved by crushing the +1/2 inch middlings to a ½-inch top size.