The problems related to development of rotational deformations of a knee joints and crack propagation in rafter elements of timber portal frames were discussed in this article. The rotational displacement, which develops between the rafter and column members due to the bending deformations of the bolts in the knee joint with a simultaneous embedment into the wood, increases the global deformations of the portal frame. Additionally, to axial force and bending moment the rafter elements are heavily loaded with shear force at the sections near knee joint especially. All effects together create very complicated complex of affecting factors. In the current study the design methodology of timber portal frames has been revised with the purpose to develop a more comprehensive set of design conditions for timber portal frames with dowel type fasteners in the knee joints. It is suggested to use the Hoffman failure criterion taking into account the difference of strength in tension and compression to manage the effects of plastic yielding combined with the crack development in wood assumed it as an orthotropic material. It has been proved by case studies of timber portal frames under service loads, as well as by tests and theoretical considerations. The set of design conditions must be supplement by additional clauses comprising Hoffman failure criterion regarding timber sections heavily loaded in shear and cross grain tension. Also, it is recommended that the design capacity of dowel type fastener should be decreased when shear force transferred by the bolt acts perpendicular to the grain direction inducing tension cross grain direction. Other measure may be application of some surface strengthening method.