Serious deficiencies in ground characterization, analysis and design at engineering works can occur when working with bimrocks (block-in-matrix rocks) and bimsoils (block-in-matrix soils). Since the 1990s, serious technical problems at engineering works performed in bimrocks/bimsoils spurred practical research, which revealed that the behavior of these geomaterials is directly related to the volumetric block proportions (VBPs). However, the way that VBPs can be confidently and correctly estimated remains an ongoing critical issue that still frustrates designers, contractors and owners. Stereological techniques can be applied to overcome this challenge by inferring 3D block contents from in situ 1D and 2D measurements, but the estimates have often been demonstrated to be erroneous. This paper presents findings from a computer-aided reinvestigation, revalidation and extension of Medley’s work of 1997 and subsequent researchers to provide approachable yet statistically robust methods to limit the uncertainty associated with estimates of 3D VBPs generated from 1D boring/scanline measurements. To this aim, a specialized Matlab code was created and virtual drilling programs were performed through 3D computer-generated bimrock models. Supported by extensive statistical-based investigations, a design chart is provided that updates and extends Medley’s 1999 chart relating uncertainty in estimates of VBP as a function of total boring/scanline lengths.