The large, directional stimuli-response of aligned liquid crystalline elastomers (LCEs) could enable functional utility in robotics, medicine, consumer goods, and photonics. The alignment of LCEs has historically been realized via mechanical alignment of a two-stage reaction. Recent reports widely utilize chain extension reactions of liquid crystal monomers (LCM) to form LCEs that are subject to either surface-enforced or mechanical alignment. Here, we prepare LCEs that contain intra-mesogenic supramolecular bonds synthesized via direct free-radical chain transfer photopolymerization processible by a distinctive mechanical alignment mechanism. The LCEs were prepared by the polymerization of a benzoic acid monomer (11OBA), which dimerized to form a liquid crystal monomer, with a diacrylate LCM (C6M). The incorporation of the intra-mesogenic hydrogen bonds increases the achievable nematic order from mechanical programming. Accordingly, LCEs prepared with larger 11OBA concentration exhibit higher magnitude thermomechanical strain values when compared to a LCE containing only covalent bonds. These LCEs can be reprogrammed with heat to return the aligned film to the polydomain state. The LCE can then be subsequently programmed to orient in a different direction. The facile preparation of (re)programmable LCEs with supramolecular bonds opens new avenues for the implementation of these materials as shape deployable elements.