The reversible ring-opening polymerization (ROP) of 1,2-dithiolanes offers a versatile dynamic chemistry platform to design materials inherent in dynamic properties. Due to the dynamic covalent nature of disulfide bonds, the ROP of 1,2-dithiolanes can be triggered by several methodologies to control the architectures and self-assembly of the resulting polymers. This Highlight Review focuses on the recent advances in developing the methodologies to make and break (recycle) the polymers of 1,2-dithiolanes. The reversible ring-opening polymerization (ROP) of 1,2-dithiolanes offers a versatile dynamic chemistry platform to design materials inherent in dynamic properties. Due to the dynamic covalent nature of disulfide bonds, the ROP of 1,2-dithiolanes can be triggered by several methodologies to control the architectures and self-assembly of the resulting polymers. This Highlight Review focuses on the recent advances in developing the methodologies to make and break (recycle) the polymers of 1,2-dithiolanes.