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Most of drilling hole problems are attributed to wellbore stability issues which adversely cause excessive lost time and cost millions of dollars. The past drilling experiences in Kupal oilfield showed excessive mud losses, kick flows, tight holes and pipe stuck leading to repeated reaming, fishing and sidetracking. Most of the drilling-associated problems in this field occurred during drilling the 12 ¼-in. hole, which is across the non-reservoir Gachsaran formation (consisting of anhydrite, gypsum and marl with thin limestone layers). Mainly due to the lack of required formation evaluation data, no geomechanical studies of this formation have been conducted to date. In this work, first, we constructed a geomechanical model to investigate the root of the problems. This is a pioneer wellbore stability work for such a complex lithology formation which included finding the equations best-matching with core data and field observations. Finally, to overcome the field challenges and hole problems, the study proposes some field remedial actions. The results of the geomechanical modeling show that the pore pressure, shear and tensile failure gradients are greatly variable with the safe mud weight window becoming excessively narrow at some intervals. This accounts for the encountered wellbore stability issues as managing the mud weight in these situations requires several casing strings. To mitigate the extent of the problem, this study proposes the application of innovative drilling technologies including casing while drilling to eliminate the casing running time with potential reduction in drilling time, and continuous circulation system to prevent cuttings settling and kick flows during connections. These technologies are capable of elimination of the geomechanical part of the drilling delay (30% of the average 77 drilling days) per well.