The currently unmeasured triple Higgs coupling is one of the strong motivations for future physics programs at the LHC and beyond. A sufficiently precise measurement can lead to qualitative changes in our understanding of electroweak symmetry breaking and the cosmological history of the Higgs potential. As such, the quantitative measurement of this coupling is now one of the benchmark measurements for any proposed collider. We study the capability of a potential 27 TeV HE-LHC upgrade in measuring the Higgs trilinear coupling via the di-Higgs production process in the bbaa channel. We emphasize that a key background from single Higgs production via gluon fusion has been underestimated and underappreciated in prior studies. We perform a detailed study taking into account two different potential detector scenarios, and validate against HL-LHC projections from ATLAS. We find that the di-Higgs production process can be observed at >= 4.5 sigma, corresponding to a ∼40% measurement of the Higgs self-coupling, with 15/ab of data at the HE-LHC.