Full-culm bamboo has been used for millennia in construction. Specific connections are normally required to suit its unique morphology and nonuniform structure. Presently, the use of full-culm bamboo is limited in the construction industry as a result of a lack of information and test standards about the use and evaluation of full-culm connections. This study aims to further explore this area by investigating the failure modes in bamboo bolt connections in uniaxial tension by considering fiber direction in finite element analysis. Three types of bolt configurations of varying permutations, namely, single, dual, and orthogonal, were investigated. An orthotropic material was used as a constitutive model in finite element formulation to capture the inhomogeneity prevailing in bamboo culm. From the strain-field analysis of a hollow-inhomogeneous model representing bamboo, shear-out failure was dominant, as a localized area equivalent to the bolt diameter was affected due to high material orthotropy with high axial strength but weak radial and tangential strength. Bearing failure is assumed to precede shear-out failure at the bolt–bamboo contact interface, as the embedding strength was affected by localized strain concentration. The strain distribution in various bolt arrangements was found to vary between bolted connections of inhomogeneous-hollow geometry of bamboo and the ones of inhomogeneous-solid geometry representing timber. The observation in this study highlights the need for alternative design criteria to specifically assess the damage mechanism in bamboo connections.