As the field of unimolecular electronics develops, there is growing interest in the development of functionalised molecular wires, such as switches, which will allow for more complex molecular-scale circuits. To this end, a three redox state single molecule switch, 1, based on bis(pyrrolo)tetrathiafulvalene (BPTTF) has been designed, synthesised and investigated using scanning tunnelling microscopy break junction (STM-BJ) studies and quantum transport calculations. Oxidising the BPTTF unit increases its conjugation, which was anticipated to increase the molecular conductance of 1. By changing the redox state of 1 electrochemically it was possible to vary the single molecule conductance by more than an order of magnitude (from 10−5.2G0 to 10−3.8G0). Simulations afforded a qualitatively similar trend. An additional, higher conductance feature is present in most traces at junction sizes of around 2.0 nm – further extension affords the switchable lower conductance feature at junction sizes closer to the molecular length (ca. 3.0 nm). Analysis of the conductance traces shows that these two conductance features occur sequentially in nearly all junctions. This behaviour is attributed to an alternative initial junction conformation in which one or more of the BPTTF sulfur atoms acts as an anchoring group. This hypothesis is supported by a computational study of binding conformations and STM-BJ studies on a model compound, 2, with only one thiol anchor. Our results indicate that the redox properties of BPTTF make it an excellent candidate for use in single molecule switches.