The emerging field of free-electron quantum optics enables electron-photon entanglement and holds the potential for generating nontrivial photon states for quantum information processing. Although recent experimental studies have entered the quantum regime, rapid theoretical developments predict that qualitatively unique phenomena only emerge beyond a certain interaction strength. It is thus pertinent to identify the maximal electron-photon interaction strength and the materials, geometries, and particle energies that enable one to approach it. We derive an upper limit to the quantum vacuum interaction strength between free electrons and single-mode photons, which illuminates the conditions for the strongest interaction. Crucially, we obtain an explicit energy selection recipe for electrons and photons to achieve maximal interaction at arbitrary separations and identify two optimal regimes favoring either fast or slow electrons over those with intermediate velocities. We validate the limit by analytical and numerical calculations on canonical geometries and provide near-optimal designs indicating the feasibility of strong quantum interactions. Our findings offer fundamental intuition for maximizing the quantum interaction between free electrons and photons and provide practical design rules for future experiments on electron-photon and electron-mediated photon-photon entanglement. They should also enable the evaluation of key metrics for applications such as the maximum power of free-electron radiation sources and the maximum acceleration gradient of dielectric laser accelerators.