This pilot study tests the reliability of laser scanning confocal microscopy (LSCM) to quantitatively measure wear on experimental obsidian tools. To our knowledge, this is the first use of confocal microscopy to study wear on stone flakes made from an amorphous silicate like obsidian. Three-dimensional surface roughness or texture area scans on three obsidian flakes used on different contact materials (hide, shell, wood) were documented using the LSCM to determine whether the worn surfaces could be discriminated using area-scale analysis, specifically relative area (RelA). When coupled with the F-test, this scale-sensitive fractal analysis could not only discriminate the used from unused surfaces on individual tools, but was also capable of discriminating the wear histories of tools used on different contact materials. Results indicate that such discriminations occur at different scales. Confidence levels for the discriminations at different scales were established using the F-test (mean square ratios or MSRs). In instances where discrimination of surface roughness or texture was not possible above the established confidence level based on MSRs, photomicrographs and RelA assisted in hypothesizing why this was so. SCANNING 33: 279–293, 2011. © 2011 Wiley Periodicals, Inc.