Reintroducing recycled plastics into production processes can lead to irreversible degradation and changes in their properties, thereby limiting their recycling potential to a finite number of loops. This study investigates the impact of process-induced degradation resulting from multiple reprocessing cycles on specific material properties and aims to establish structure–property relationships. Four different polyolefins, including two polypropylenes, high-density polyethylene, and low-density polyethylene, were selected for the study. The materials underwent extrusion, pelletizing, injection molding, and milling before being reintroduced into the reprocessing cycle. This sequence of processing steps was repeated six times on each material. Various characterization techniques, including high-temperature gel permeation chromatography, melt mass flow rate, parallel-plate rheology, differential scanning calorimetry, gas chromatography–mass spectrometry, and optical defect control system, were performed to evaluate the molecular structure, rheological behavior, thermal stability, and the resulting contaminants and defects after each reprocessing step. The reprocessing of polypropylene resulted in a gradual decrease in the average molecular weights accompanied by a shift to lower viscosities and higher melt mass flow rates, whereas the polyethylene grades showed the opposite trend with a less pronounced effect in high-density polyethylene. The volatile organic compounds rose in polypropylene and sank in polyethylene after reprocessing. Additionally, all four materials exhibited an increase in degradation-related defects based on optical defect analysis.Graphical abstract