With increasing environmental concerns, the building sector must rethink the selection of building materials not only for structural members but also for connections. Densified wooden nails might become an alternative to metallic fasteners, at least in applications with lower structural requirements. However, their structural behaviour in timber-to-timber connections is not yet systematically studied. This paper presents a series of 90 shear tests to explore the shear capacity and slip modulus of timber-to-timber connections with wooden nails. Specimens with different nail dimensions, different nail orientations, and different nail arrangements were investigated. A typical three-member push-out test setup was adopted where the wooden nails were oriented perpendicular or inclined to the shear plane. Specimens with inclined nails exposed to shear and tensile forces showed a higher shear resistance due to the activated tensile capacity of the wooden nails. Failure of the wooden nails was predominantly observed when the nails were loaded in tension. This means that the interface between the wooden nails and the timber did not fail. Based on the results from the shear tests, an analytical model was developed to predict the load bearing capacity of timber-to-timber connections exposed to bending stresses. The analytical model was validated with experimental investigations.