Systems of mutually coupled oscillators with delay coupling are of great interest for various applications in electronics, laser physics, biophysics, etc. Time delay usually originates from the finite speed of propagation of the coupling signal. In this paper, we present the results of detailed bifurcation analysis of two delay-coupled limit-cycle (Landau–Stuart) oscillators. First, we study the simplified case when the delay time is much smaller than the oscillation build-up time. When the coupling signal propagates between the two counterparts, it acquires a phase shift, which strongly affects the synchronization pattern. Depending on this phase shift, the system may demonstrate the behavior typical for either dissipative or conservative (reactive) coupling. We examine stability of the in-phase and anti-phase synchronous states and reveal the complicated pattern of the synchronization domains on the frequency mismatch—coupling strength parameter plane paying a special attention to the mechanisms of appearance and disappearance of the phase multistability. We demonstrate that taking into account reactive phase nonlinearity the coupling signal acquires an additional phase shift, which depends on the signal intensity. We also examine the more complicated case of finite delay time. The increase of the reactive nonlinearity parameter and the delay time leads to transformations of synchronization domains similar to those that occur when the phase shift increases. For the bifurcation analysis, we employ XPPAUT and DDEBifTool package and verify the results by direct numerical integration.