We investigate the dynamical interaction between cosmic rays (CRs) and the multiphase interstellar medium (ISM) using numerical magnetohydrodynamic (MHD) simulations with a two-moment CR solver and TIGRESS simulations of star-forming galactic disks. We previously studied the transport of CRs within TIGRESS outputs using a “postprocessing” approach, and we now assess the effects of the MHD backreaction to CR pressure. We confirm our previous conclusion that there are three quite different regimes of CR transport in multiphase ISM gas, while also finding that simulations with “live MHD” predict a smoother CR pressure distribution. The CR pressure near the midplane is comparable to other pressure components in the gas, but the scale height of CRs is far larger. Next, with a goal of understanding the role of CRs in driving galactic outflows, we conduct a set of controlled simulations of the extraplanar region above z = 500 pc, with imposed boundary conditions flowing from the midplane into this region. We explore a range of thermal and kinematic properties for the injected thermal gas, encompassing both hot, fast-moving outflows, and cooler, slower-moving outflows. The boundary conditions for CR energy density and flux are scaled from the supernova rate in the underlying TIGRESS model. Our simulations reveal that CRs efficiently accelerate extraplanar material if the latter is mostly warm/warm-hot gas, in which CRs stream at the Alfvén speed, and the effective sound speed increases as density decreases. In contrast, CRs have very little effect on fast, hot outflows where the Alfvén speed is small, even when the injected CR momentum flux exceeds the injected MHD momentum flux.