We investigate the evolution of entanglement within an open, strongly coupled system interacting with a heat bath as its environment, in the frameworks of both the doubly holographic model and the Sachdev-Ye-Kitaev (SYK) model. Generally, the entanglement within the system initially increases as due to internal interactions; however, it eventually dissipates into the environment. In the doubly holographic setup, we consider an end-of-the-world brane in the bulk to represent an eternal black hole coupled with its radiation and the evolution of the global thermofield double (TFD) state. For small black holes, the reflected entropy between the bipartition exhibits a ramp-plateau-slump behavior, where the plateau arises due to the phase transition of the entanglement wedge cross-section before the Page time. Similarly, the mutual information between the bipartition displays a ramp-slop-stabilizing behavior. In quantum mechanics, we consider a double copy of the SYK-plus-bath system in a global TFD state, resembling an eternal black hole interacting with an environment. The Rényi mutual information within the double-copied SYK clusters exhibits a ramp-plateau-slope-stabilizing behavior. The dynamic behaviors of the entanglement quantities observed in these two models are attributable to the competition between the internal interaction of the system and the external interaction with the baths. Our study provides a fine-grained picture of the entanglement dynamics inside black holes before their Page time.