In underground mining, many miners are injured or lose their lives because of roof/pillar instability each year, and this is a persistent safety risk. Characterization of overlying strata is important for the design of safe and cost-effective ground support systems. Entry roof characterization can be performed by geological back-mapping of the ground using various methods such as geophysical logging, borescoping, rock mass rating, and intelligent roof bolt drilling systems. This paper offers a brief review of mine roof characterization methods, followed by an introduction to and discussion of roof characterization methods using instrumented roof bolters. A brief overview of the various instrumentation systems developed for roof bolt drills is presented. The results of the preliminary study and initial testing indicate that, despite recent improvements in the area of ground characterization by instrumented drills, there are still several issues that must be addressed to improve the efficiency and accuracy of existing systems. A summary of suggested improvements is provided.