We study non-Markovian dynamics of an open quantum system system interacting with a nonstationary squeezed bosonic reservoir. We derive exact and approximate descriptions for the open system dynamics. Focusing on the spin boson model, we compare exact dynamics with Redfield theory and a quantum optical master equation for both short and long time dynamics and in non-Markovian and Markov regimes. The squeezing of the bath results in asymptotic oscillations in the stationary state, which are captured faithfully by the Redfield master equation in the case of weak coupling. Furthermore, we find that the bath squeezing direction modifies the effective system–environment coupling strength and, thus, the strength of the dissipation.