Well integrity is critical to the safety and success of subsurface energy exploration and management, as leakage of fluids from subsurface reservoirs is often induced by compromised wells. This study investigates bending deformation of a mockup of an oil/gas well that is subjected to loads expected in deviated wells under reservoir compaction and assesses the feasibility of utilizing distributed fiber optic strain sensing to monitor the deformation. A well mockup, which consists of outer and inner steel pipes with a cemented annulus, is tested under three-point bending loading and its strain and curvature development is monitored by Brillouin optical time domain reflectometry/analysis (BOTDR/A) as well as optical frequency domain reflectometry (OFDR). The primary objective of this research is to assess the strain sensing performance of newly fabricated fiber optic cables and to identify key cable characteristics which could improve the quality of distributed strain measurements with BOTDR/A. Results show that the tight-buffered cable is best suited for strain sensing as its maximum errors in the strain measurement were −36% and −24% against conventional sensors at the maximum elastic and plastic bending loads, respectively, whereas those of the non-tight-buffered cable were −45% and −71%, respectively. Similar trends were obtained in the bending curvature measurement. The detailed design of the tight-buffered cable is presented to elucidate key characteristics of such a cable, which will facilitate accurate distributed strain sensing in oil and gas wells.