ABSTRACT The interstellar medium is threaded by a hierarchy of filaments from large scales (∼100 pc) to small scales (∼0.1 pc). The masses and lengths of these nested structures may reveal important constraints for cloud formation and evolution, but it is difficult to investigate from an evolutionary perspective using single observations. In this work, we extract simulated molecular clouds from the ‘Cloud Factory’ galactic-scale ISM suite in combination with 3D Monte Carlo radiative transfer code polaris to investigate how filamentary structure evolves over time. We produce synthetic dust continuum observations in three regions with a series of snapshots and use the filfinder algorithm to identify filaments in the dust derived column density maps. When the synthetic filaments mass and length are plotted on an mass–length (M–L) plot, we see a scaling relation of L ∝ M0.45 similar to that seen in observations, and find that the filaments are thermally supercritical. Projection effects systematically affect the masses and lengths measured for the filaments, and are particularly severe in crowded regions. In the filament M–L diagram we identify three main evolutionary mechanisms: accretion, segmentation, and dispersal. In particular we find that the filaments typically evolve from smaller to larger masses in the observational M–L plane, indicating the dominant role of accretion in filament evolution. Moreover, we find a potential correlation between line mass and filament growth rate. Once filaments are actively star forming they then segment into smaller sections, or are dispersed by internal or external forces.