The environmental issues surrounding plastics and their end-oflife disposal (e.g., plastic pollution, circular economy, and microplastics) has resulted in a significant desire for degradable polymers. Particularly, there is a large focus on finding alternatives to common hydrophobic polymers (e.g., polyethylene). However, alternatives also need to be found for hydrophilic polymers, such as, polyacrylamide (PAAm), which is widely used in biomedical, agricultural, and waste-treatment applications. With this drive for degradability, there is renewed interest in radical ring-opening copolymerisation (rROP) as a way of introducing degradability to vinyl polymers through the integration of cleavable bonds. A popular group of rROP monomers are cyclic ketene acetals (CKA). Recently we, and others, demonstrated that these monomers could be copolymerised with a variety of vinyl monomers. These copolymers showed extremely efficient degradation under various conditions (PBS, basic, etc.) However, CKAs have significant drawbacks: (i) low reactivity towards common vinyl monomers (e.g., acrylates, sterenics, acrylamides etc.), consequently, requiring a large excess of CKA present in the copolymerisation; (ii) a significant proportion of ring-retained CKAs are produced during polymerisation, resulting in nondegradable acetal units in the copolymer backbone and (iii) they are easily hydrolysed in protic solvents or by traces of water severely limiting potential polymerisation conditions. As an alternative to CKAs, thionolactones have been reported as a new class of cyclic monomers capable of undergoing rROP via a thiocarbonyl-addition-ring opening (TARO) mechanism. The rROP of thionolactones with vinyl monomers enables the insertion of labile thioester groups into the copolymer backbone. Recently we reported rROP of the thionolactone dibenzo[c,e]oxepane-5-thione (DOT) with industrially relevant isoprene (I) as well as the conventional emulsion copolymerisation with n-butyl acrylate and styrene. In these cases, DOT displayed superior reactivity towards the vinyl monomers used and excellent stability in protic solvents, compared to CKAs. Furthermore, these DOT-containing hydrophobic copolymers could be degraded in a variety of conditions including in the presence of physiologically relevant concentrations of cysteine or glutathione, and thus these copolymers can be considered for use in nanomedicine. Additionally, Bingham et al. demonstrated that DOT can be terpolymerised with dimethylacrylamide and Nisopropylacrylamide (NIPAAm) producing degradable copolymers with a tuneable lower critical solution temperature (LCST). However, the majority of these copolymers were not water-soluble at all temperatures.