Measuring the Higgs self-coupling at the LHC has proven to be extremely challenging in the Standard Model, making such a measurement a primary target for future 100 TeV colliders. We explore an alternative scenario, where the LHC is upgraded to 27 TeV — the so-called “High-Energy” (HE)-LHC. We demonstrate the capabilities of such a 27 TeV proton collider at measuring the Higgs self-coupling via di-Higgs production in the bb¯γγ channel. Our projections are based on a full simulation of the detector performance using Delphes, based on the current projected performance for the ATLAS detector at HL-LHC, with simulations of all signal and relevant backgrounds. We find that a 5σ discovery of di-Higgs production is possible at a 27 TeV collider, which corresponds to a ∼40% measurement of the trilinear coupling in the bb¯γγ channel alone.