Highwall mining involves driving a series of parallel entries with web pillars in between. These entries are driven by using a continuous miner with attached conveying system to extract locked up coal behind the highwall slope when the open cut coal mine reaches its ultimate limit. These entries are driven unmanned, unventilated and unsupported. Therefore, a detailed knowledge of structural features ahead of operations is essential in assessing the stability of these entries. Highwall mining operations can greatly benefit from accurate structural mapping of rock mass defects. The stability of these entries can be suitably assessed for any major roof failure by adopting discrete fracture network based structural modelling to characterize and delineate the regions of possible major roof failures to prevent damage to the conveyor and burial of the expensive continuous miner. In this paper, a generalized framework is described based on photogrammetric survey, digital mapping and discrete fracture network based structural modelling to characterise such failures for an Indian highwall mining operation. A sensitivity analysis is undertaken to demonstrate the significance of structure persistence in the geotechnical assessment. Such analysis would provide more insight into designing highwall mining layouts and in predicting possible impending highwall failures, and indirectly facilitates reducing machine downtime for better management of highwall mining operations.