The aim of the study was to create and verify a theoretical model for single-shear steel to bamboo nailed connections in natural bamboo. To this end, existing timber strength and fracture theories were used to model the brittle and ductile failure strength of the studied bamboo connection. Experimental tests of steel to bamboo nailed connection subjected to short-term loading in single shear parallel to fibre direction in Moso bamboo confirmed the suitability of the timber models to predict the connection behaviour. The findings constitute a basis for development of theory for screws, which is the advocated connector type by the authors. It is anticipated that the predictability of bamboo dowelled connection behaviour, along with the latest developments in bamboo design standardization, will enhance the designers confidence to implement dowelled bamboo connections in practice.