The kinetics of Criegee intermediates are important for atmospheric modeling. However, the quantitative kinetics of Criegee intermediates are still very limited, especially for those with hydroxy groups. Here, we calculate rate constants for the unimolecular reaction ofE-glycolaldehyde oxide [E-hydroxyethanal oxide,E-(CH2OH)CHOO], for its reactions with H2O and (H2O)2, and for the reaction of theE-(CH2OH)CHOO…H2O complex with H2O. For the highest level of electronic structure, we use W3X-L//CCSD(T)-F12a/cc-pVDZ-F12 for the unimolecular reaction and the reaction with water and W3X-L//DF-CCSD(T)-F12b/jun-cc-pVDZ for the reaction with 2 water molecules. For the dynamics, we use a dual-level strategy that combines conventional transition state theory with the highest level of electronic structure and multistructural canonical variational transition state theory with small-curvature tunneling with a validated density functional for the electronic structure. This dynamical treatment includes high-frequency anharmonicity, torsional anharmonicity, recrossing effects, and tunneling. We find that the unimolecular reaction ofE-(CH2OH)CHOO depends on both temperature and pressure. The calculated results show thatE-(CH2OH)CHOO…H2O + H2O is the dominant entrance channel, while previous investigations only considered Criegee intermediates + (H2O)2. In addition, we find that the atmospheric lifetime ofE-(CH2OH)CHOO with respect to 2 water molecules is particularly short with a value of 1.71 × 10−6s at 0 km, which is about 2 orders of magnitude shorter than those usually assumed for Criegee intermediate reactions with water dimer. We also find that the OH group inE-(CH2OH)CHOO enhances its reactivity.