Quantum chemistry calculations using hybrid density functional theory and the coupled-cluster method have been performed to investigate the ring-opening pathways in the oxidation of morpholine (1-oxa-4-aza-cyclohexane). Hydrogen abstraction can form two different carbon-centered radicals, morpholin-2-yl or morpholin-3-yl, or the nitrogen-centered radical, morpholin-4-yl, none of which are found to have low-energy pathways to ring-opening. Extensive exploration of multiple reaction pathways following molecular oxygen addition to these three radicals revealed two competitive low energy pathways to ring-opening. Addition of O(2) to either carbon-centered radical, followed by a 1,4-H shifting mechanism can yield a long-lived cyclic epoxy intermediate, susceptible to ring-opening, following further radical attack. In particular, the second pathway begins with O(2) attack on morpholin-2-yl, followed by a 1,5-H shift and a unimolecular ring-opening without having to overcome a high barrier, releasing a significant amount of heat in the overall ring-opening reaction. The calculations provide valuable context for the development of mechanisms for the low temperature combustion chemistry of nitrogen and oxygen-containing fuels.