Considering two non-interacting qubits in the context of open quantum systems, it is well known that their common environment may act as an entangling agent. In a perturbative regime the influence of the environment on the system dynamics can effectively be described by a unitary and a dissipative contribution. For the two-spin Boson model with (sub-) Ohmic spectral density considered here, the particular unitary contribution (Lamb shift) easily explains the buildup of entanglement between the two qubits. Furthermore it has been argued that in the adiabatic limit, adding the so-called counterterm to the microscopic model compensates the unitary influence of the environment and, thus, inhibits the generation of entanglement. Investigating this assertion is one of the main objectives of the work presented here. Using the hierarchy of pure states (HOPS) method to numerically calculate the exact reduced dynamics, we find and explain that the degree of inhibition crucially depends on the parameter s determining the low frequency power law behavior of the spectral density J(ω)∼ω^s exp(−ω/ω_c). Remarkably, we find that for resonant qubits, even in the adiabatic regime (arbitrarily large ω_c), the entanglement dynamics is still influenced by an environmentally induced Hamiltonian interaction. Further, we study the model in detail and present the exact entanglement dynamics for a wide range of coupling strengths, distinguish between resonant and detuned qubits, as well as Ohmic and deep sub-Ohmic environments. Notably, we find that in all cases the asymptotic entanglement does not vanish and conjecture a linear relation between the coupling strength and the asymptotic entanglement measured by means of concurrence. Further we discuss the suitability of various perturbative master equations for obtaining approximate entanglement dynamics.