Shaping free-electron wave functions with light enables powerful capabilities for exploring ultrafast and quantum phenomena in electron microscopes. In such interactions, the electron velocity is commonly assumed to remain constant, while recoil effects accumulate through free-space propagation of wave-function components with different momenta, ultimately producing a temporal comb of electron wave packets. Here, we explore regimes in which recoil becomes relevant already during the interaction, modifying phase matching and producing qualitatively different electron dynamics. The resulting electron states enable stronger temporal compression than can be achieved when recoil is neglected during the interaction. These results advance our understanding of quantum electron–light interactions and open new routes for ultrafast electron-beam shaping.