Low molecular weight additives which can cooperatively self-assemble with supramolecular polyurethanes via complementary hydrogen bonding interactions offer an attractive route to enhancing the properties of addressable polymer networks. Here, we present the design, synthesis, characterisation and mechanical properties of a series of supramolecular polyurethanes with varied loadings of a low molecular weight bis-urea additive. These additives are able to self-assemble with analogous recognition motifs within the supramolecular polyurethanes to form polar 'hard' domains, promoting phase separation within the material and, crucially, increasing the strength of the polymer network. In addition, the bis-urea additive is a by-product within the polymerisation and thus can be synthesised in situ, without the need for complex purification or blending. The mechanical properties of these reinforced polymers were enhanced when compared to the pristine supramolecular polyurethane alone, as a result of higher degrees of order within the polymer matrix. Furthermore, a formulation comprising the small molecule blended with the supramolecular polyurethane was produced to examine the effect of material preparation and filler dispersion within the polymer matrix. Interestingly, the mechanical performance of a blended material was diminished as a result of modest dispersion and incorporation within the polymer matrix. These findings thus demonstrate a facile, one-pot, method that does not require purification to produce reinforced supramolecular polyurethanes. This methodology may find use in industrial applications in which enhancements to the physical and mechanical properties can be easily achieved through the in situ synthesis of low molecular weight additives within the polymerisation.