In conclusion, we have developed a straightforward synthesis of a novel difunctionalized strained TCO with cargo-releasing capabilities in only four high yielding steps. The acetylated iodohydrin intermediate and the subsequent elimination reaction were key steps in this pathway to afford the TCOs in excellent yields. To our knowledge this is the shortest reported synthesis of difunctionalized TCOs with releasing properties allowing improved access to these click reagents for both diagnostic and therapeutic applications. Furthermore, because of the high yields and the continuous photoflow isomerization process our pathway is amenable for larger scale synthesis. The TCOs have two orthogonal handles so that derivatization with different moieties is possible, while the allylic alcohol enables release of a payload upon click reaction with a tetrazine derivative, as demonstrated with carbonate and carbamate linked cargo molecules, even in a cellular environment. Moreover, we identified a TCO that fully retains the allylic moiety upon the click reaction. This product may be valuable for non-releasable applications requiring stable conjugates with orthogonal handles on the TCO. The broad range applicability of the TCO-tetrazine click and release system combined with this efficient synthetic accessibility will in our view strongly contribute to new in vitro and in vivo biomedical applications in the near future.