The present research was aimed at finding out the relative effect of advancement in photocopier technology on the analysis of handwriting line quality features in multi-generational photocopies. Five subsequent multi-generational photocopies of 50 signature samples from different individuals which were produced by 75 black and white photocopiers were used for line quality assessments. Variations in line quality features in different photocopy generations, such as: smooth edges or ragged edges, broken or continuous stroke, fine tapering changes, and some identification details of features like pen lifts, retouching, and hesitation were carefully observed in sample photocopies, which were recorded according to the brand and model of photocopier machines, as well as their size and speed. The results of the study revealed that raggedness in line was often observed in third generation (G3) and higher generations, in samples produced by some low speed copiers (copying speed < 30 cpm) or very high speed copiers (copying speed ≤ 80 cpm). However, their line quality was still found to be good enough for handwriting analysis up to the fifth generation (G5) in photocopy samples produced by some medium speed copiers (copying speed 30 to 50 cpm). It was, however, observed that, usually, continuity of line and smoothness of line were appreciably lost in G3 and higher generations in photocopies which were produced by portable desktop printers. Exceptionally, certain artifacts that are usually found in some higher generation copies were conspicuously absent in all photocopy generations (G1–G5) which were produced by some advanced third generation photocopiers. Hopefully, the information obtained from the study will be found useful to document examiners when examining certain cases involving multi-generations of photocopier reproductions.