Observables related to the real part of the gravitational eikonal, such as the deflection angle and time delay, have been found so far to have a smooth post-Minkowskian (PM) expansion whose validity extends from the non-relativistic to the most extreme ultra-relativistic (UR) regime, which smoothly connects with massless particle collisions. To describe gravitational radiation, the eikonal phase has to be promoted to a unitary operator for which we motivate a proposal and start discussing properties in the soft-radiation limit. A convergent PM expansion is found to only hold below an UR bound (discussed in the GR literature in the seventies) above which a different expansion is instead needed implying, in general, some non-analyticity in Newton's constant. In this extreme UR regime soft radiative observables receive contributions only from gravitons and are therefore universal. This generalises the pattern discussed in [1] beyond the elastic case.