The precise construction of polyfunctional molecules remains a topic of great interest. Many targets of value are densely functionalized and are comprised of several contiguous stereocenters. The ring-opening of epoxides is an attractive method for the assembly of alcohol-containing stereoarrays. Our laboratory has a programmatic focus on the use of unusual nucleophiles for the ring-opening of both transient and stable electrophiles. As part of this line of inquiry, it occurred to us that a ring-opening of epoxides by pendant sulfamates and sulfamides would offer predictable access to vicinal amino-alcohols and would complement our previous efforts with intramolecular cleavage of aziridines by di-tert-butyl-silanol auxiliaries. There is no shortage of interesting amino-alcohols, and new methods for their construction are valuable. Unfortunately, a simple intermolecular aminolysis of epoxides often leads to intractable mixtures of regioisomeric products (Scheme 1A). Many creative investigators have developed "temporary tethering" approaches for the regioselective opening of epoxides with N-nucleophiles (Scheme 1B). Nevertheless, even with chelating Lewis acids, depending on the substrate, a mixture of regioisomers can still result. Covalent tethering offers a complementary approach (Scheme 1C). While a synthetic step must be expended to attach the tether, the subsequent cyclization is often highly regioselective and diastereoselective. To our surprise, cleaving epoxides with covalently tethered N-nucleophiles has not been extensively investigated. Sporadic reports exist with carbamate and acetamidate nucleophiles. Here, we detail our efforts to develop the first cleavage of epoxides by pendant sulfamates and sulfamides.