Abstract The diversity of Type II supernovae (SNe II) is thought to be driven mainly by differences in their progenitor’s hydrogen-rich (H-rich) envelope mass, with SNe IIP having long plateaus (∼100 days) and the most massive H-rich envelopes. However, it is an ongoing mystery why SNe II with short plateaus (tens of days) are rarely seen. Here, we present optical/near-infrared photometric and spectroscopic observations of luminous Type II short-plateau SNe 2006Y, 2006ai, and 2016egz. Their plateaus of about 50–70 days and luminous optical peaks (≲−18.4 mag) indicate significant pre-explosion mass loss resulting in partially stripped H-rich envelopes and early circumstellar material (CSM) interaction. We compute a large grid of MESA+STELLA single-star progenitor and light-curve models with various progenitor zero-age main-sequence (ZAMS) masses, mass-loss efficiencies, explosion energies, ⁵⁶Ni masses, and CSM densities. Our model grid shows a continuous population of SNe IIP–IIL–IIb-like light-curve morphology in descending order of H-rich envelope mass. With large ⁵⁶Ni masses (≳0.05 M _⊙), short-plateau SNe II lie in a confined parameter space as a transitional class between SNe IIL and IIb. For SNe 2006Y, 2006ai, and 2016egz, our findings suggest high-mass red supergiant (RSG) progenitors (M _ZAMS ≃ 18–22 M _⊙) with small H-rich envelope masses ( ) that have experienced enhanced mass loss ( ) for the last few decades before the explosion. If high-mass RSGs result in rare short-plateau SNe II, then these events might ease some of the apparent underrepresentation of higher-luminosity RSGs in observed SN II progenitor samples.