Solid waste and leachate samples from bench-scale anaerobic bioreactors and flushing bioreactors (FBs), containing mature waste were characterized using Fourier Transform Infrared Spectroscopy (FTIR) to provide a better understanding of the changes in waste characteristics when waste transitions from mature to stabilized. Humic acid (HA) extracted from mature waste and waste removed from the FBs were characterized using FTIR and 13C nuclear magnetic resonance. FBs were operated under three different treatment scenarios (flushing with clean water, recirculation of leachate treated by chemical oxidation, and recirculation of leachate treated by chemical oxidation with waste aeration. FTIR spectra of FB waste and leachate supported the stabilization of waste that occurred after the additional treatment. There was a shift in the dominance of organic to inorganic functional groups when compared to changes in conventional parameters that aligned with published values on waste stability. HA extracted from the mature waste were dominated by aliphatic carbon and aromatic carbon was less intense. Treatment by flushing resulted in a decrease in aliphatic carbon and an increase in aromatic carbon. HA extracted from reactors with oxidized leachate recirculation and aeration decreased in aliphatic carbon content, with minimal change in aromatic carbon. Therefore, the additional treatment did not result in an increase in the reactivity potential of the HA which aligns with FTIR and principal component analysis. Results suggest that spectroscopic techniques could be used to assess the stability of waste samples as opposed to more time-consuming analyses.