The longwall system is an extraction system commonly used in coal mining in many countries, including Poland. One of the methods for reducing extraction costs is the dual use of the gateroad. In the first instance, the gateroad serves as the tailgate, and during the exploitation of the second coal panel, it functions as the headgate. Such a situation requires maintenance of the roadway behind the longwall face, which is typically challenging, due to significant stress-related loads on the support and its substantial deformation. The support design for this kind of roadway should take into consideration the dual impact of exploitation pressure and the caved zone influence behind the longwall face. This article presents the results of in-situ research conducted on two roadways behind the longwall face. In both roadways, the effectiveness of specially designed steel arch frames and rock bolt patterns were examined to minimize roadway deformations and maintain their functionality. The research project was comprised of several stages. Initially, mining and laboratory studies were conducted to determine the geomechanical parameters of the rocks. Subsequently, excavation stability and functionality forecasts were performed based on the authors’ empirical indicators. Then, numerical analyses were carried out to design support schemes (steel arches and rock bolt) in both roadways. A fully automated monitoring system with programmed data loggers was designed to check the behaviour of a specific rock mass and the support elements. The load on the steel arch support was measured with the help of load cells, while the load on the rock bolt support was carried out with the help of measurement bolts. Behind the longwall face, the loads on the wooden cribs set from the goaf side were also monitored. Additionally, the measurement station was equipped with extensometers to monitor the movement of roof layers and stress meters to determine changes in rock mass stress. Laser scanning or traditional surveying methods were also used to verify the support schemes through roadway convergence measurements. The obtained results allowed us to draw conclusions regarding the optimization of support schemes and to give recommendations for the practical application of specific reinforcements in excavations maintained behind the longwall face.