Bisphenol A-based epoxy thermosets involve both environmental and health risks. By reacting a vegetal oil-based epoxide with an aromatic diacid containing S−S bonds a thermoset is produced. Herein, reprocessable thermosets were synthesized, the recyclability being designed through a dual mechanism: that of disulfide metathesis and of transesterifications. To assess the feasibility of the reprocessing, a series of 10 initiators was tested to probe their effect not only on the cross-linking reaction but also on the recyclability. This study introduces for the first time the key role of the initiator on the material performance and on their reprocessing. A very good reprocessability was obtained for thermosets prepared using as initiator the imidazole. Moreover, the thermosets exhibit complete chemical recyclability in 1 N NaOH at 80°C, after 3 days, without needing additional chemicals. The reprocessed materials have similar performance with the virgin ones, even after 10 cycles of reprocessing.