Additive manufacturing is a relatively new technology that is already widely applied in engineering and has a great potential to be implemented in the footwear industry. Indeed, significant improvements in the quality of 3D printed parts contribute to the quality enhancements on additive manacling in footwear industries, and the fabrication of insole is one of them. This article presents the design and development of anatomical insole and highlights its printing challenges using BFlex material applying a customized Fused Deposition Modelling (FDM) printer. The dimension of the designed insole has a length and width of 300 mm and 107 mm, respectively and it has a thickness of 15.6 mm at the heel and 5 mm at the toe. The main challenges faced during the fabrication of the desired insole are build orientation, poor adhesion of the print bed, and oscillations of the printing object at top layers. Experimental results showed that the vertical orientation of the insole, 20% infill, and support structure with 15 degrees overhang angle significantly increased the printing performance.