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Understanding the dynamics of dissipative quantum systems, particularly beyond the weak coupling approximation, is central to various quantum applications. While numerically exact methods provide accurate solutions, they often lack the analytical insight provided by theoretical approaches. In this study, we employ the recently developed method dubbed the effective Hamiltonian theory to understand the dynamics of system–bath configurations without resorting to a perturbative description of the system–bath coupling energy. Through a combination of mapping steps and truncation, the effective Hamiltonian theory offers both analytical insights into signatures of strong couplings in open quantum systems and a straightforward path for numerical simulations. To validate the accuracy of the method, we apply it to two canonical models: a single spin immersed in a bosonic bath and two noninteracting spins in a common bath. In both cases, we study the transient regime and the steady state limit at nonzero temperature and spanning system–bath interactions from the weak to the strong regime. By comparing the results of the effective Hamiltonian theory with numerically exact simulations, we show that although the former overlooks non-Markovian features in the transient equilibration dynamics, it correctly captures non-perturbative bath-generated couplings between otherwise non-interacting spins, as observed in their synchronization dynamics and correlations. Altogether, the effective Hamiltonian theory offers a powerful approach for understanding strong coupling dynamics and thermodynamics, capturing the signatures of such interactions in both relaxation dynamics and in the steady state limit. [ABSTRACT FROM AUTHOR]