During Run I and Run II of the LHC great progress has been made in establishing many of the properties of the Higgs boson. However, important aspects of the Higgs sector, such as the Higgs self-coupling, remain only poorly constrained by current data. The detailed exploration of the Higgs sector will therefore be one of the key tasks of the physics program at the HL-HE LHC. Focusing on di-Higgs production in gluon-fusion, we will discuss some of the recent theoretical and experimental progress in understanding this process as well as the challenges going forward. The prospects for constraining the Higgs self-coupling using the proposed HL and HE upgrades at LHC will be reviewed.