Barrier pillars and gateroads play a vital role for the safe exploitation of coal from the panel in the longwall workings. The barrier pillars and gateroads are subjected to the front abutment and side abutment loads during the retreat of the panel. These structures may fail if the developed load on them is higher than their strength. The stability of the longwall structures such as barrier, gateroads and face is paramount in extracting the coal from the panel safely. For this, a deep longwall mine in India is chosen for the study using a 3D numerical modelling technique. In this paper, three critical conditions such as scenario 1 (no side goaved-out panel), scenario 2 (with side goaved-out panel) and scenario 3 (with two side goaved-out panels) are taken. For each scenario, five retreat distances such as 100, 125, 150, 175 and 200 m are considered for detailed investigation. The development of vertical displacement in gateroads, vertical stresses on barriers, vertical stress concentration factor, abutment zone and yield zone for longwall face are extracted and analyzed. Also, the safety factor of the barrier and longwall face is estimated considering the Hoek-Brown rock mass failure criterion. From the study, it is observed that the maximum vertical displacement of 121 mm in TG3 at scenario 3 for a retreat distance of 200 m and a minimum vertical displacement of 33 mm in TG2 for a retreat distance of 100 m at scenario 2. The development of vertical stress on the barrier is found to be between 8.78 and 13.40 MPa, and the safety factor of the barrier lies in between 1.56 and 1.80. The study also revealed that the yield zone at the longwall face lies within 2 to 3 m.