The implementation of engineered mass timber products in construction and the proliferation of computer numerical control machinery, as a technically feasible and economically justifiable fabrication technique, have given rise to new methods of construction. Inspired by traditional carpentry connections, digital fabrication is harnessed to establish connections between engineered timber panels in freeform systems through interlocking mechanisms, without supplementary metal connectors. This paper characterizes the behavior of digitally-fabricated Through-Tenon connections subjected to bending moments, which are critical in freeform timber plate structures. Six timber specimen groups, made from hardwood Laminated Veneer Lumber, are designed according to material and assembly properties. The moment–rotation behavior of the specimens is documented and evaluated in qualitative (i.e., slip modulus, strength, ductility) and quantitative measures (i.e., damage propagation, failure mode). Overall, the specimens reach their maximum strength soon after yielding occurs regardless of their fiber orientation or assembly pattern. Furthermore, all specimens are classified as having low ductility. The yield and maximum strengths, associated rotations, and joint stiffness depends on the tab assembly vector. For the fiber-perpendicular specimens, the damage modes are independent of the assembly vector. On the other hand, the damage propagation and failure mechanisms strongly depend on the insertion angle for the fiber-parallel specimens.