A conformationally flexible calix[4]pyrrole possessing a conjugated electronic structure (an N-substituted oxoporphyrinogen (OxP) related to porphyrin) was used to investigate the influence of mechanical stretching on the single-molecule conductance of these molecules using the mechanically-controlled break junction (MCBJ) technique. The results show that the molecule can be immobilized in a single-molecule break junction configuration, giving rise to different behaviours. These include step-like features in the conductance vs. displacement traces as well as conductance traces that exhibit a slower decay (‘downhill’ traces) than measured for direct tunneling. The latter class of traces can be associated with the mechanical manipulation (i. e., stretching) of the molecule with inter-electrode distances as long as 2 nm. Density functional theory (DFT) calculations reveal that OxP molecules are stable under stretching in the length regime studied.