The detection of gravitational wave signals in recent years from the mergers of binaries comprised of neutron stars and black holes has raised pressing questions about the formation of these binary compact object systems and the characteristics of their progenitors. As one of the key progenitors for these systems, it has become paramount to understand the fate of massive interacting binary stars. In order for binary neutron star/black hole systems to merge in a Hubble time, the pair must undergo a common envelope (CE) phase to dramatically reduce the separation distance of the progenitors prior to CE ejection. The standard treatment for CE is a decades-old energy formalism which relies on an efficiency term and simple energy budget criterion for envelope ejection, but it is well known that this prescription fails to explain how high mass stellar binaries can evolve into compact object binaries that are close enough to merge. Supported by insights from local and global computational simulations, we present significant updates to this energy framework for predicting the outcomes of these systems.