In heavy-ion collisions, nuclear matter is subjected to extreme conditions in a highly dynamical, rapidly evolving environment. This poses a tremendous challenge for calculating jet quenching observables. Current approaches rely on analytical results for static cases, introducing theoretical uncertainties and biases in our understanding of the pre-equilibrated medium. To address this issue, we employ resummation schemes to derive analytical rates for radiative energy loss in generic, evolving backgrounds. We investigate regimes where rare scattering and multiple scattering with the dynamical medium occurs, and extract relevant scales governing the in-medium emission rate of soft gluons. Our analysis indicates that strong jet quenching is only possible when the equilibration time of the medium is longer than its mean free path, highlighting the importance of medium modifications of jets in the earliest stages of heavy-ion collisions. We also demonstrate analytically that a medium evolution, which initially has a small coupling to jets, typically leads to a stronger jet azimuthal asymmetry at the same jet suppression factor.