Roof falls are currently one of the most dangerous threats associated with underground mining at great depth. Every occurrence of such an event poses a significant risk to the mining crew and disturbs the continuity of the mining process, which clearly affects the economy of the exploitation process. The development of a reliable monitoring system may significantly reduce the impact of eventual roof failure and will have a positive effect on the sustainability of the extraction process. Within this research study, a prototype of an instrumented rock bolt developed for continuous stress measurement is presented. The procedure of a 4-groove multilevel instrumented rock bolt is described and the calibration process is shown. Then, preliminary results of long-term in situ monitoring are presented. Based on the continuous monitoring of stress distribution within immediate roof strata, it was concluded that the developed instrumented rock bolt provides reliable results and is a very useful device, ensuring the possibility of early warning for miners about increasing roof fall risk.